tert-butyl N-(2-phenylethyl)carbamate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-BOC-2-phenylethylamine (3.1 g) and 5% rhodium on alumina (1.1 g) are combined in methanol (40 ml) containing acetic acid (1.0 ml). The mixture is shaken under hydrogen at 50 psi for about 20 hours. The mixture is filtered, evaporated in vacuo, and the residue taken up into ethyl acetate. The organic solution is washed with water, 5% sodium bicarbonate solution, water, brine, dried over sodium sulfate, filtered, and evaporated in vacuo to give N-BOC-2-cyclohexylethylamine. The mixture is filtered evaporated in vacuo The organic solution is washed with water, 5% sodium bicarbonate solution, water, brine dried over sodium sulfate filtered evaporated in vacuo

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Combine N-t-butoxycarbonyl-2-phenyl-ethylamine (22.1 g, 100 mmol) and THF (100 mL) under an inert atmosphere. Cool to 0° C. in an ice-bath. Add portionwise sodium hydride (0.206 g, 110 mmol) and allow to stir until hydrogen evolution ceases. Add allyl bromide (9.50 mL, 110 mmol) and warm to ambient temperature. Cool again to 0° C. in an ice-bath. Add sodium hydride (0.92 g, 40 mmol) and allow to stir until hydrogen evolution ceases. Add allyl bromide (3.0 mL, 35.0 mmol) and heat to reflux for 18 hours. Cool to ambient temperature. Add a saturated aqueous solution of ammonium chloride (200 mL) and extract with ethyl acetate. Dry the organic layer over MgSO4, filter, and evaporate in vacuo. Chromatograph eluting sequentially with hexane and 10% ethyl acetate/hexane to give the title compound. Cool again to 0° C. in an ice-bath to reflux for 18 hours Cool to ambient temperature extract with ethyl acetate Dry the organic layer over MgSO4 filter evaporate in vacuo Chromatograph eluting sequentially with hexane and 10% ethyl acetate/hexane

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Combine N-t-butoxycarbonyl-2-phenyl-ethylamine (22.1 g, 100 mmol) and THF (100 mL) under an inert atmosphere. Cool to 0° C. in an ice-bath. Add portionwise sodium hydride (0.206 g, 110 mmol) and allow to stir until hydrogen evolution ceases. Add allyl bromide (9.50 mL, 110 mmol) and warm to ambient temperature. Cool again to 0° C. in an ice-bath. Add sodium hydride (0.92 g, 40 mmol) and allow to stir until hydrogen evolution ceases. Add allyl bromide (3.0 mL, 35.0 mmol) and heat to reflux for 18 hours. Cool to ambient temperature. Add a saturated aqueous solution of ammonium chloride (200 mL) and extract with ethyl acetate. Dry the organic layer over MgSO4, filter, and evaporate in vacuo. Chromatograph eluting sequentially with hexane and 10% ethyl acetate/hexane to give the title compound. Cool again to 0° C. in an ice-bath to reflux for 18 hours Cool to ambient temperature extract with ethyl acetate Dry the organic layer over MgSO4 filter evaporate in vacuo Chromatograph eluting sequentially with hexane and 10% ethyl acetate/hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-BOC-2-phenylethylamine (3.1 g) and 5% rhodium on alumina (1.1 g) are combined in methanol (40 ml) containing acetic acid (1.0 ml). The mixture is shaken under hydrogen at 50 psi for about 20 hours. The mixture is filtered, evaporated in vacuo, and the residue taken up into ethyl acetate. The organic solution is washed with water, 5% sodium bicarbonate solution, water, brine, dried over sodium sulfate, filtered, and evaporated in vacuo to to give N-BOC-2-cyclohexylethylamine. The mixture is filtered evaporated in vacuo The organic solution is washed with water, 5% sodium bicarbonate solution, water, brine dried over sodium sulfate filtered evaporated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-BOC-2-phenylethylamine (3.1 g) and 5% rhodium on alumina (1.1 g) are combined in methanol (40 ml) containing acetic acid (1.0 ml). The mixture is shaken under hydrogen at 50 psi for about 20 hours. The mixture is filtered, evaporated in vacuo, and the residue taken up into ethyl acetate. The organic solution is washed with water, 5% sodium bicarbonate solution, water, brine, dried over sodium sulfate, filtered, and evaporated in vacuo to to give N-BOC-2-cyclohexylethylamine. The mixture is filtered evaporated in vacuo The organic solution is washed with water, 5% sodium bicarbonate solution, water, brine dried over sodium sulfate filtered evaporated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-BOC-2-phenylethylamine (3.1 g) and 5% rhodium on alumina (1.1 g) are combined in methanol (40 ml) containing acetic acid (1.0 ml). The mixture is shaken under hydrogen at 50 psi for about 20 hours. The mixture is filtered, evaporated in vacuo, and the residue taken up into ethyl acetate. The organic solution is washed with water, 5% sodium bicarbonate solution, water, brine, dried over sodium sulfate, filtered, and evaporated in vacuo to give N-BOC-2-cyclohexylethylamine. The mixture is filtered evaporated in vacuo The organic solution is washed with water, 5% sodium bicarbonate solution, water, brine dried over sodium sulfate filtered evaporated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-BOC-2-phenylethylamine (3.1 g) and 5% rhodium on alumina (1.1 g) are combined in methanol (40 ml) containing acetic acid (1.0 ml). The mixture is shaken under hydrogen at 50 psi for about 20 hours. The mixture is filtered, evaporated in vacuo, and the residue taken up into ethyl acetate. The organic solution is washed with water, 5% sodium bicarbonate solution, water, brine, dried over sodium sulfate, filtered, and evaporated in vacuo to give N-BOC-2-cyclohexylethylamine. The mixture is filtered evaporated in vacuo The organic solution is washed with water, 5% sodium bicarbonate solution, water, brine dried over sodium sulfate filtered evaporated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-BOC-2-phenylethylamine (3.1 g) and 5% rhodium on alumina (1.1 g) are combined in methanol (40 ml) containing acetic acid (1.0 ml). The mixture is shaken under hydrogen at 50 psi for about 20 hours. The mixture is filtered, evaporated in vacuo, and the residue taken up into ethyl acetate. The organic solution is washed with water, 5% sodium bicarbonate solution, water, brine, dried over sodium sulfate, filtered, and evaporated in vacuo to give N-BOC-2-cyclohexylethylamine. The mixture is filtered evaporated in vacuo The organic solution is washed with water, 5% sodium bicarbonate solution, water, brine dried over sodium sulfate filtered evaporated in vacuo

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Combine N-t-butoxycarbonyl-2-phenyl-ethylamine (22.1 g, 100 mmol) and THF (100 mL) under an inert atmosphere. Cool to 0° C. in an ice-bath. Add portionwise sodium hydride (0.206 g, 110 mmol) and allow to stir until hydrogen evolution ceases. Add allyl bromide (9.50 mL, 110 mmol) and warm to ambient temperature. Cool again to 0° C. in an ice-bath. Add sodium hydride (0.92 g, 40 mmol) and allow to stir until hydrogen evolution ceases. Add allyl bromide (3.0 mL, 35.0 mmol) and heat to reflux for 18 hours. Cool to ambient temperature. Add a saturated aqueous solution of ammonium chloride (200 mL) and extract with ethyl acetate. Dry the organic layer over MgSO4, filter, and evaporate in vacuo. Chromatograph eluting sequentially with hexane and 10% ethyl acetate/hexane to give the title compound. Cool again to 0° C. in an ice-bath to reflux for 18 hours Cool to ambient temperature extract with ethyl acetate Dry the organic layer over MgSO4 filter evaporate in vacuo Chromatograph eluting sequentially with hexane and 10% ethyl acetate/hexane

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Combine N-t-butoxycarbonyl-2-phenyl-ethylamine (22.1 g, 100 mmol) and THF (100 mL) under an inert atmosphere. Cool to 0° C. in an ice-bath. Add portionwise sodium hydride (0.206 g, 110 mmol) and allow to stir until hydrogen evolution ceases. Add allyl bromide (9.50 mL, 110 mmol) and warm to ambient temperature. Cool again to 0° C. in an ice-bath. Add sodium hydride (0.92 g, 40 mmol) and allow to stir until hydrogen evolution ceases. Add allyl bromide (3.0 mL, 35.0 mmol) and heat to reflux for 18 hours. Cool to ambient temperature. Add a saturated aqueous solution of ammonium chloride (200 mL) and extract with ethyl acetate. Dry the organic layer over MgSO4, filter, and evaporate in vacuo. Chromatograph eluting sequentially with hexane and 10% ethyl acetate/hexane to give the title compound. Cool again to 0° C. in an ice-bath to reflux for 18 hours Cool to ambient temperature extract with ethyl acetate Dry the organic layer over MgSO4 filter evaporate in vacuo Chromatograph eluting sequentially with hexane and 10% ethyl acetate/hexane

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Combine N-t-butoxycarbonyl-2-phenyl-ethylamine (22.1 g, 100 mmol) and THF (100 mL) under an inert atmosphere. Cool to 0° C. in an ice-bath. Add portionwise sodium hydride (0.206 g, 110 mmol) and allow to stir until hydrogen evolution ceases. Add allyl bromide (9.50 mL, 110 mmol) and warm to ambient temperature. Cool again to 0° C. in an ice-bath. Add sodium hydride (0.92 g, 40 mmol) and allow to stir until hydrogen evolution ceases. Add allyl bromide (3.0 mL, 35.0 mmol) and heat to reflux for 18 hours. Cool to ambient temperature. Add a saturated aqueous solution of ammonium chloride (200 mL) and extract with ethyl acetate. Dry the organic layer over MgSO4, filter, and evaporate in vacuo. Chromatograph eluting sequentially with hexane and 10% ethyl acetate/hexane to give the title compound. Cool again to 0° C. in an ice-bath to reflux for 18 hours Cool to ambient temperature extract with ethyl acetate Dry the organic layer over MgSO4 filter evaporate in vacuo Chromatograph eluting sequentially with hexane and 10% ethyl acetate/hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phenethyl-carbamic acid tert-butyl ester (1107 mg, 5.0 mmol) is dissolved in dry DMF (7.75 ml). To this solution, sodium hydride (60% w/w in oil, 302 mg, 7.55 mmol) is added under vigorous stirring and stirring is continued for 30 min. Then 1-chloro-3-iodo-propane (250 mg, 5.0 mmol) is dropped into the solution followed by stirring for 2 h at rt and another hour at 50° C. After switching off the heating and addition of sodium 1H-benzoimidazole-2-thiolate (1722 mg, 10 mmol) the mixture is allowed to stir overnight at rt. All the DMF is evaporated in vacuo and the remaining crude is dissolved in DCE. This organic phase is washed twice with water, dried over Na2SO4 and evaporated to give the crude product which is purified by flash chromatography on silica gel (AcOEt/heptane, 1:9 to 1:1), yielding the title compound (289 mg) in 14% as a colourless oil: tR=2.24 min (LC-2), ESI-MS (pos.): m/z 412.43 [M+H]+, MS (neg.): m/z 410.46 [M−H]+; 1H-NMR (CDCl3): δ (ppm) 1.48 (s, 9H, tBu), 1.89 (br. s, 2H, SCH2CH2), 2.83 (t, 2H, PhCH2CH2N), 3.09 (br. s, 2H), 3.26 (br. s, 1H), 3.42 (t, 2H, PhCH2CH2N), 3.47 (br. s, 2H), 7.13-7.30 (m, 7Harom), 7.52 (m, 2H). stirring by stirring for 2 h at rt and another hour at 50° C to stir overnight at rt All the DMF is evaporated in vacuo the remaining crude is dissolved in DCE This organic phase is washed twice with water dried over Na2SO4 evaporated to give the crude product which is purified by flash chromatography on silica gel (AcOEt/heptane, 1:9 to 1:1)