N-cyclohexyl-2,4-dihydroxy-3,3-dimethylbutanamide

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Place N-cyclohexyl-2,4-dihydroxy-3,3-dimethyl-butyramide (2.178 g, 9.51 mmol), triethylamine (2.7 ml, 19.31 mmol) and toluenesulfonyl chloride (3.70 g, 19.21 mmol) in CH2Cl2 (50 mL) at 0° C. Stir for 30 minutes at 0° C. Quench with hexane and warm to room temperature. Filter white precipitate. Strip the solvent and dissolve the residue in 40 ml of dry THF under the nitrogen atmosphere. Add sodium hydride (3.4 g, 85 mmol) and stir at room temperature for 12 hours. Quench the reaction with methanol/water mixture. Extract with ethyl acetate. Wash the extract with brine and dry over magnesium sulfate. Purification by flash chromatography affords 1.25 g (36%) of the title compound: Mass spectrum (apci) m/z=366 (M+H). at 0° C Quench with hexane warm to room temperature Filter white precipitate Strip the solvent and dissolve the residue in 40 ml of dry THF under the nitrogen atmosphere Quench the reaction with methanol/water mixture Extract with ethyl acetate Wash the extract with brine dry over magnesium sulfate Purification by flash chromatography

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

Procedure: Place N-cyclohexyl-2,4-dihydroxy-3,3-dimethyl-butyramide (2.178 g, 9.51 mmol), triethylamine (2.7 ml, 19.31 mmol) and toluenesulfonyl chloride (3.70 g, 19.21 mmol) in CH2Cl2 (50 mL) at 0° C. Stir for 30 minutes at 0° C. Quench with hexane and warm to room temperature. Filter white precipitate. Strip the solvent and dissolve the residue in 40 ml of dry THF under the nitrogen atmosphere. Add sodium hydride (3.4 g, 85 mmol) and stir at room temperature for 12 hours. Quench the reaction with methanol/water mixture. Extract with ethyl acetate. Wash the extract with brine and dry over magnesium sulfate. Purification by flash chromatography affords 1.25 g (36%) of the title compound: Mass spectrum (apci) m/z=366 (M+H). at 0° C Quench with hexane warm to room temperature Filter white precipitate Strip the solvent and dissolve the residue in 40 ml of dry THF under the nitrogen atmosphere Quench the reaction with methanol/water mixture Extract with ethyl acetate Wash the extract with brine dry over magnesium sulfate Purification by flash chromatography

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

Procedure: Place N-cyclohexyl-2,4-dihydroxy-3,3-dimethyl-butyramide (2.178 g, 9.51 mmol), triethylamine (2.7 ml, 19.31 mmol) and toluenesulfonyl chloride (3.70 g, 19.21 mmol) in CH2Cl2 (50 mL) at 0° C. Stir for 30 minutes at 0° C. Quench with hexane and warm to room temperature. Filter white precipitate. Strip the solvent and dissolve the residue in 40 ml of dry THF under the nitrogen atmosphere. Add sodium hydride (3.4 g, 85 mmol) and stir at room temperature for 12 hours. Quench the reaction with methanol/water mixture. Extract with ethyl acetate. Wash the extract with brine and dry over magnesium sulfate. Purification by flash chromatography affords 1.25 g (36%) of the title compound: Mass spectrum (apci) m/z=366 (M+H). at 0° C Quench with hexane warm to room temperature Filter white precipitate Strip the solvent and dissolve the residue in 40 ml of dry THF under the nitrogen atmosphere Quench the reaction with methanol/water mixture Extract with ethyl acetate Wash the extract with brine dry over magnesium sulfate Purification by flash chromatography

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Place 2-hydroxy-3,3-dimethyl-cyclopentanone (1.044 g, 7.86 mmol), cyclohexylamine (1.91 ml, 16.51 mmol) and toluenesulfonic acid monohydrate (0.152 g, 0.1 mmol) in EtOH (4 mL) in a microwave reactor. Stir for 1 hour at 150° C. Quench with 1N HCl and extract with ethyl acetate. Wash the extract with NaHCO3, brine. Dry over magnesium sulfate, filter, and concentrate to afford N-cyclohexyl-2,4-dihydroxy-3,3-dimethyl-butyramide. Quench with 1N HCl extract with ethyl acetate Wash the extract with NaHCO3, brine Dry over magnesium sulfate filter concentrate

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Place 2-hydroxy-3,3-dimethyl-cyclopentanone (1.044 g, 7.86 mmol), cyclohexylamine (1.91 ml, 16.51 mmol) and toluenesulfonic acid monohydrate (0.152 g, 0.1 mmol) in EtOH (4 mL) in a microwave reactor. Stir for 1 hour at 150° C. Quench with 1N HCl and extract with ethyl acetate. Wash the extract with NaHCO3, brine. Dry over magnesium sulfate, filter, and concentrate to afford N-cyclohexyl-2,4-dihydroxy-3,3-dimethyl-butyramide. Quench with 1N HCl extract with ethyl acetate Wash the extract with NaHCO3, brine Dry over magnesium sulfate filter concentrate