tert-butyl N-[2-(benzylamino)ethyl]carbamate

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

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

Procedure: To a mixture of tert-butyl 2-(benzylamino)ethylcarbamate (2.8 g, 11.2 mmol) and 37% aqueous CH2O (1.0 mL, 11.2 mmol) in 1,2-dicholoroethane (35 mL) at RT was added NaHB(AcO)3 (3.7 g, 11.2 mmol). The mixture was stirred (RT, 16 h), diluted with saturated aqueous NaHCO3 (400 ml) and extracted with EA (3×300 ml). The organic layer was dried over MgSO4 and concentrated under reduced pressure to afford tert-butyl 2-(benzyl(methyl)amino)ethylcarbamate (1.38 g, 46.8%). 1HNMR (CDCl3): δ7.25 (m, 5H, CH), 3.5 (s, 2H, CH2), 3.3 (m, 2H, CH2), 2.48 (m, 2H, CH2), 2.2 (s, 3H, CH3), 1.4 (s, 9H, CH3). extracted with EA (3×300 ml) The organic layer was dried over MgSO4 concentrated under reduced pressure

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

Procedure: To a solution of tert-butyl 2-aminoethylcarbamate (3.7 g, 22.3 mmol), benzaldehyde (2.36 g, 22.3 mmol) and MgSO4 (1.33 g) in 1,2-dicholoroethane (300 mL) and Et3N (3.1 mL, 22.3 mmol) at RT was added NaHB(AcO)3. The mixture was stirred (RT, 16 h) and filtered. The solution was washed with saturated NaHCO3 (200 ml), dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel, eluting with MeOH-DCM (0-10%) to afford tert-butyl 2-(benzylamino)ethylcarbamate (1.4 g, 23%). Mass calculated for C14H22N2O2=250.34. found: [M+H]+=251.3. filtered The solution was washed with saturated NaHCO3 (200 ml) dried over MgSO4 concentrated under reduced pressure The crude product was purified by chromatography on silica gel eluting with MeOH-DCM (0-10%)

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

Procedure: To a solution of tert-butyl 2-aminoethylcarbamate (3.7 g, 22.3 mmol), benzaldehyde (2.36 g, 22.3 mmol) and MgSO4 (1.33 g) in 1,2-dicholoroethane (300 mL) and Et3N (3.1 mL, 22.3 mmol) at RT was added NaHB(AcO)3. The mixture was stirred (RT, 16 h) and filtered. The solution was washed with saturated NaHCO3 (200 ml), dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel, eluting with MeOH-DCM (0-10%) to afford tert-butyl 2-(benzylamino)ethylcarbamate (1.4 g, 23%). Mass calculated for C14H22N2O2=250.34. found: [M+H]+=251.3. filtered The solution was washed with saturated NaHCO3 (200 ml) dried over MgSO4 concentrated under reduced pressure The crude product was purified by chromatography on silica gel eluting with MeOH-DCM (0-10%)

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

Procedure: To a mixture of tert-butyl 2-(benzylamino)ethylcarbamate (2.8 g, 11.2 mmol) and 37% aqueous CH2O (1.0 mL, 11.2 mmol) in 1,2-dicholoroethane (35 mL) at RT was added NaHB(AcO)3 (3.7 g, 11.2 mmol). The mixture was stirred (RT, 16 h), diluted with saturated aqueous NaHCO3 (400 ml) and extracted with EA (3×300 ml). The organic layer was dried over MgSO4 and concentrated under reduced pressure to afford tert-butyl 2-(benzyl(methyl)amino)ethylcarbamate (1.38 g, 46.8%). 1HNMR (CDCl3): δ7.25 (m, 5H, CH), 3.5 (s, 2H, CH2), 3.3 (m, 2H, CH2), 2.48 (m, 2H, CH2), 2.2 (s, 3H, CH3), 1.4 (s, 9H, CH3). extracted with EA (3×300 ml) The organic layer was dried over MgSO4 concentrated under reduced pressure

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

Procedure: To a solution of tert-butyl 2-aminoethylcarbamate (3.7 g, 22.3 mmol), benzaldehyde (2.36 g, 22.3 mmol) and MgSO4 (1.33 g) in 1,2-dicholoroethane (300 mL) and Et3N (30.1 mL, 22.3 mmol) at RT was added NaHB(AcO)3. The mixture was stirred (RT, 16 h) and filtered. The solution was washed with saturated NaHCO3 (200 ml), dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel, eluting with MeOH-DCM (0-10%) to afford tert-butyl 2-(benzylamino)ethylcarbamate (1.4 g, 23%). Mass calculated for C14H22N2O2=250.34. found: [M+H]+=251.3. filtered The solution was washed with saturated NaHCO3 (200 ml) dried over MgSO4 concentrated under reduced pressure The crude product was purified by chromatography on silica gel eluting with MeOH-DCM (0-10%)

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

Procedure: To a mixture of tert-butyl 2-(benzylamino)ethylcarbamate (2.8 g, 11.2 mmol) and 37% aqueous CH2O (1.0 mL, 11.2 mmol) in 1,2-dicholoroethane (35 mL) at RT was added NaHB(AcO)3 (3.7 g, 11.2 mmol). The mixture was stirred (RT, 16 h), diluted with saturated aqueous NaHCO3 (400 ml) and extracted with EA (3×300 ml). The organic layer was dried over MgSO4 and concentrated under reduced pressure to afford tert-butyl 2-(benzyl(methyl)amino)ethylcarbamate (1.38 g, 46.8%). 1HNMR (CDCl3): δ7.25 (m, 5H, CH), 3.5 (s, 2H, CH2), 3.3 (m, 2H, CH2), 2.48 (m, 2H, CH2), 2.2 (s, 3H, CH3), 1.4 (s, 9H, CH3). extracted with EA (3×300 ml) The organic layer was dried over MgSO4 concentrated under reduced pressure

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

Procedure: To a mixture of tert-butyl 2-(benzylamino)ethylcarbamate (2.8 g, 11.2 mmol) and 37% aqueous CH2O (1.0 mL, 11.2 mmol) in 1,2-dicholoroethane (35 mL) at RT was added NaHB(AcO)3 (3.7 g, 11.2 mmol). The mixture was stirred (RT, 16 h), diluted with saturated aqueous NaHCO3 (400 ml) and extracted with EA (3×300 ml). The organic layer was dried over MgSO4 and concentrated under reduced pressure to afford tert-butyl 2-(benzyl(methyl)amino)ethylcarbamate (1.38 g, 46.8%). 1HNMR (CDCl3): δ7.25 (m, 5H, CH), 3.5 (s, 2H, CH2), 3.3 (m, 2H, CH2), 2.48 (m, 2H, CH2), 2.2 (s, 3H, CH3), 1.4 (s, 9H, CH3). extracted with EA (3×300 ml) The organic layer was dried over MgSO4 concentrated under reduced pressure

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

Procedure: To a solution of tert-butyl 2-aminoethylcarbamate (3.7 g, 22.3 mmol), benzaldehyde (2.36 g, 22.3 mmol) and MgSO4 (1.33 g) in 1,2-dicholoroethane (300 mL) and Et3N (3.1 mL, 22.3 mmol) at RT was added NaHB(AcO)3. The mixture was stirred (RT, 16 h) and filtered. The solution was washed with saturated NaHCO3 (200 ml), dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel, eluting with MeOH-DCM (0-10%) to afford tert-butyl 2-(benzylamino)ethylcarbamate (1.4 g, 23%). Mass calculated for C14H22N2O2=250.34. found: [M+H]+=251.3. filtered The solution was washed with saturated NaHCO3 (200 ml) dried over MgSO4 concentrated under reduced pressure The crude product was purified by chromatography on silica gel eluting with MeOH-DCM (0-10%)

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

Procedure: To a mixture of tert-butyl 2-(benzylamino)ethylcarbamate (2.8 g, 11.2 mmol) and 37% aqueous CH2O (1.0 mL, 11.2 mmol) in 1,2-dicholoroethane (35 mL) at RT was added NaHB(AcO)3 (3.7 g, 11.2 mmol). The mixture was stirred (RT, 16 h), diluted with saturated aqueous NaHCO3 (400 ml) and extracted with EA (3×300 ml). The organic layer was dried over MgSO4 and concentrated under reduced pressure to afford tert-butyl 2-(benzyl(methyl)amino)ethylcarbamate (1.38 g, 46.8%). 1HNMR (CDCl3): δ7.25 (m, 5H, CH), 3.5 (s, 2H, CH2), 3.3 (m, 2H, CH2), 2.48 (m, 2H, CH2), 2.2 (s, 3H, CH3), 1.4 (s, 9H, CH3). extracted with EA (3×300 ml) The organic layer was dried over MgSO4 concentrated under reduced pressure

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

Procedure: To a solution of tert-butyl 2-aminoethylcarbamate (3.7 g, 22.3 mmol), benzaldehyde (2.36 g, 22.3 mmol) and MgSO4 (1.33 g) in 1,2-dicholoroethane (300 mL) and Et3N (30.1 mL, 22.3 mmol) at RT was added NaHB(AcO)3. The mixture was stirred (RT, 16 h) and filtered. The solution was washed with saturated NaHCO3 (200 ml), dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel, eluting with MeOH-DCM (0-10%) to afford tert-butyl 2-(benzylamino)ethylcarbamate (1.4 g, 23%). Mass calculated for C14H22N2O2=250.34. found: [M+H]+=251.3. filtered The solution was washed with saturated NaHCO3 (200 ml) dried over MgSO4 concentrated under reduced pressure The crude product was purified by chromatography on silica gel eluting with MeOH-DCM (0-10%)

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

Procedure: Benzaldehyde (3.3 ml, 32.4 mmol) was added to a stirred solution of tert-butyl-N-(2-aminoethyl)carbamate (5.19 g, 32.4 mmol) in 1,2-dichloroethane (50 ml). After stirring for 1 h sodium triacetoxyborohydride (10.3 g, 48.6 mmol) was added in two portions and the reaction mixture stirred at room temperature for a further 3 h. Dichloromethane (300 ml) was added and the mixture washed with 1N sodium hydroxide. The organic layer was dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed on silica gel eluting with 50-100% ethyl acetate in hexane then 1-5% methanol in ethyl acetate to afford the title compound (4.9 g, 60%). Mass spectrum (AP+): Found 251 (MH+). C14H22N2O2 requires 250. was added in two portions the mixture washed with 1N sodium hydroxide The organic layer was dried (Na2SO4) evaporated in vacuo The residue was chromatographed on silica gel eluting with 50-100% ethyl acetate in hexane