Sodium borohydride → trans-1-(p-nitrobenzyloxycarbonyl)-4-hydroxy-L-proline p-methoxybenzyl ester

HRID 893170Notes

Reaction equation

HRID 893170 reaction equation
[CH3:1][O:2][C:3]1[CH:31]=[CH:30][C:6]([CH2:7][O:8][C:9](=[O:29])[C@@H:10]2[CH2:14][C:13](=[O:15])[CH2:12][N:11]2[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)=[O:17])=[CH:5][CH:4]=1.[BH4-].[Na+]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9](=[O:29])[C@@H:10]2[CH2:14][C@H:13]([OH:15])[CH2:12][N:11]2[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)=[O:17])=[CH:30][CH:31]=1.[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9](=[O:29])[C@@H:10]2[CH2:14][C@@H:13]([OH:15])[CH2:12][N:11]2[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)=[O:17])=[CH:30][CH:31]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 151163081-(p-nitrobenzyloxycarbonyl)-4-oxo-L-proline p-methoxybenzyl ester

Product 2

HCID 13504318trans-1-(p-nitrobenzyloxycarbonyl)-4-hydroxy-L-proline p-methoxybenzyl esterHCID 13504319cis-1-(p-nitrobenzyloxycarbonyl)-4-hydroxy-L-proline p-methoxybenzyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

650 mg of 1-(p-nitrobenzyloxycarbonyl)-4-oxo-L-proline p-methoxybenzyl ester was dissolved in 45 ml of ethanol, and 86 mg of sodium borohydride was added thereto in two divided portions at room temperature. After 30 minutes, the reaction mixture was concentrated under reduced pressure at 30° C. or below, and the concentrate was diluted with ethyl acetate, washed with water, dried over sodium sulfate and distilled off to remove the solvent. The residue was purified by silica gel column chromatography to obtain cis-1-(p-nitrobenzyloxycarbonyl)-4-hydroxy-L-proline p-methoxybenzyl ester (450 mg) and trans-1-(p-nitrobenzyloxycarbonyl)-4-hydroxy-L-proline p-methoxybenzyl ester (190 mg).

Workup

  1. customat room temperature
  2. concentrationthe reaction mixture was concentrated under reduced pressure at 30° C. or below
  3. additionthe concentrate was diluted with ethyl acetate
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. distillationdistilled off
  7. customto remove the solvent
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7c71974ee8c840d4839b439baf46283f
Source dataset
uspto-grants-1992_06
Patent number
US05122604

Reaction notes

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