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

HRID 1757709Notes

Reaction equation

HRID 1757709 reaction equation
[C:1]([O:5][C:6](=[O:43])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1CC(=O)[C@H](CC1C=CC=CC=1)NC(=O)[C@H](CCC(=O)N)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:43])[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 70042923HCID 70042923, compound

Product 1

HCID 6453108L-Proline 1,1-dimethylethyl ester

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

0.55 g (0.93 mmol) of N-[[N-[N-(benzyloxycarbonyl)-L-glutaminyl]-L-phenylalanyl]methyl]-L-proline tert.butyl ester, prepared as described in Example 6, was reduced in 15 ml of isopropanol in the presence of 90 mg of sodium borohydride as described in Example 7. After working-up, the product was chromatographed on silica gel using 2% methanol in chloroform for the elution. There were obtained 60 mg of isomer 1 of N-[3(S)-[[N-(benzyloxycarbonyl)-L-glutaminyl]amino]-2(R or S)-hydroxy-4-phenylbutyl]-L-proline tert.butyl ester in the form of a solid; Rf (System B): 0.37; MS: m/e 597 [M+H]+, and 65 mg of isomer 2in the form of a solid; Rf (System B): 0.25; MS: m/e 597 [M+H]+.

Workup

  1. customthe product was chromatographed on silica gel using 2% methanol in chloroform for the elution

Sources & evidence

ORD record
ord-3cdb3c29ad8f41049f0446636e87b0c3
Source dataset
uspto-grants-1995_08
Patent number
US05446161

Reaction notes

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