Benzyl [(1S)-1-(4-methoxyphenyl)ethyl]carbamate → (S)-1-(4-Methoxyphenyl)ethylamine

HRID 1755812Notes

Reaction equation

HRID 1755812 reaction equation
C(OC([NH:11][C@H:12]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)[CH3:13])=O)C1C=CC=CC=1>CO.[Pd]>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C@@H:12]([NH2:11])[CH3:13])=[CH:15][CH:16]=1

Participants

4

Reactant 1

HCID 57071074Benzyl [(1S)-1-(4-methoxyphenyl)ethyl]carbamate

Product 1

HCID 793467(S)-1-(4-Methoxyphenyl)ethylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of the above (29) (42.8 g) in methanol (300 mL) was hydrogenated over 5% Pd on carbon (~2 g) at 50 psi H2 for 4 h in a Parr shaker. The product (30) was obtained after filtration of the catalyst through Celite®, rinsing with fresh methanol and evaporation (22.9 g, 100%). GC RT 4.68 min (HP 530 mμ×20 m methylsilicone column, He carrier flow rate 20 mL/min, 100° C. isothermal); 1H NMR (CDCl3) δ1.37 (3H, d, J=7 Hz), 2.25(2H, br s), 2.78(3H, s), 4.08(1H, q), 7.15(4H, q).

Sources & evidence

ORD record
ord-3d30559477484fb68dca9c391bcde77d
Source dataset
uspto-grants-1995_08
Patent number
US05438118

Reaction notes

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