(S)-[1-[[[(1,1-Dimethylethoxy)carbonyl]amino]methyl]-2-phenylethyl]carbamic acid phenylmethyl ester → (S)-tert-Butyl (2-amino-3-phenylpropyl)carbamate

HRID 582535Notes

Reaction equation

HRID 582535 reaction equation
C1(COC(=O)[NH:10][C@H:11]([CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)C=CC=CC=1>C(O)C.[Pd]>[CH3:27][C:24]([O:23][C:21](=[O:22])[NH:20][CH2:19][C@@H:11]([NH2:10])[CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)([CH3:25])[CH3:26]

Participants

4

Reactant 1

HCID 11036409(S)-[1-[[[(1,1-Dimethylethoxy)carbonyl]amino]methyl]-2-phenylethyl]carbamic acid phenylmethyl ester

Product 1

HCID 53637716(S)-tert-Butyl (2-amino-3-phenylpropyl)carbamateYield 116%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (S)-[1-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-2-phenylethyl]carbamic acid phenylmethyl ester (2.89 g,7.51 mmol) and 10% Pd-C (0.171 g) in ethanol (70 ml) was stirred under hydrogen for 2 days. The reaction mixture was filtered through celite and the filtrate was evaporated to leave the title compound (2.18 g) as a solid, nmr(δ,CDCl3) includes 1.43(s,9H), 2.5-2.62 and 2.83(m and dd,2H), 3.0 and 3.1-3.25(m,2H), 3.25-3.4(m,1H), 5.0-5.15(m,1H), 7.15-7.35(m,5H).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-e78475d626a34d819311a0cb052e4069
Source dataset
uspto-grants-1999_07
Patent number
US05925624

Reaction notes

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