Sodium borohydride → L-Proline 1,1-dimethylethyl ester

HRID 742835Notes

Reaction equation

HRID 742835 reaction equation
[C:1]([O:5][C:6](=[O:39])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1CC(=O)[C@H](CC1C=CC=CC=1)NC(=O)[C@H](C)NC(OCC1C=CC=CC=1)=O)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)(C)C>[C:1]([O:5][C:6](=[O:39])[C@@H:7]1[CH2:11][CH2:10][CH2:9][NH:8]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 70041042N-[[N-[N-(benzyloxycarbonyl)-L-alanyl]-L-phenylalanyl]-methyl]-L-proline tert.butyl ester

Product 1

HCID 6453108L-Proline 1,1-dimethylethyl ester

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

0.45 g (0.84 mmol) of N-[[N-[N-(benzyloxycarbonyl)-L-alanyl]-L-phenylalanyl]methyl]-L-proline tert.butyl ester, prepared as described in Example 5, was reduced in 15 ml of isopropanol in the presence of 80 mg of sodium borohydride as described in Example 7. After working-up the two isomers were separated by chromatography on silica gel using System A for the elution. There were obtained 70 mg of isomer 1 of N-[3(S)-[[N-(benzyloxycarbonyl)-L-alanyl]amino]-2(R or S)-hydroxy-4-phenylbutyl]-L-proline tert.butyl ester in the form of a gum; Rf (System A): 0.38; MS: m/e 540 [M+H]+ and 50 mg of isomer 2 in the form of a gum; Rf (System A) 0.21; MS: m/e 540 [M+H]+.

Workup

  1. customwere separated by chromatography on silica gel using System A for the elution

Sources & evidence

ORD record
ord-3e56aa6e138c445eb2c80e945f93290e
Source dataset
uspto-grants-1996_09
Patent number
US05554756

Reaction notes

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