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

HRID 742836Notes

Reaction equation

HRID 742836 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-(benzyloxy-carbonyl)-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 2 in 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-2dc044d3b8144e2e91d6e377e716c15d
Source dataset
uspto-grants-1996_09
Patent number
US05554756

Reaction notes

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