ethyl 7-(N-benzyloxycarbonylamino)-3-oxo-2-phenylheptanoate → ethyl 7-(N-benzyloxycarbonylamino)-3-hydroxy-2-phenylheptanoate

HRID 2392929Notes

Reaction equation

HRID 2392929 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16](=[O:29])[CH:17]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([OH:29])[CH:17]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 18980739ethyl 7-(N-benzyloxycarbonylamino)-3-oxo-2-phenylheptanoate

Product 1

HCID 18980744ethyl 7-(N-benzyloxycarbonylamino)-3-hydroxy-2-phenylheptanoateYield 65.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The same procedures as in Example 8 were performed except that 0.1 g (0.25 mmol) of ethyl 7-(N-benzyloxycarbonylamino)-3-oxo-2-phenylheptanoate and 1.4 mg (0.00125 mmol) of [RuI(p-cymene)(S)-BINAP]I were placed in an 100 ml autoclave, 2 ml of methanol was added, and the reaction was performed under a hydrogen pressure of 65 kg/cm2 for 18 hours, to prepare the target compound as a colorless oil. (Yield was 65.3%) The ratio of the syn-form to the anti-form was 87.5:12.5, and the optical purity of the syn-form was 93.2% ee.

Workup

  1. additionwas added
  2. customfor 18 hours

Sources & evidence

ORD record
ord-8b27bea212594ab581379db4f6a5a384
Source dataset
uspto-grants-1998_09
Patent number
US05801271

Reaction notes

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