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

HRID 2392930Notes

Reaction equation

HRID 2392930 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13](=[O:26])[CH:14]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([OH:26])[CH:14]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 1

HCID 54117513ethyl 7-(N-t-butoxycarbonylamino)-3-oxo-2-phenylheptanoate

Product 1

HCID 18980741ethyl 7-(N-t-butoxycarbonylamino)-3-hydroxy-2-phenylheptanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The same procedures as in Example 14 were performed except that 0.1 g (0.28 mmol) of ethyl 7-(N-t-butoxycarbonylamino)-3-oxo-2-phenylheptanoate, 6.2 mg (0.0056 mmol) of [RuI(p-cymene)(S)-BINAP]I, 9.2 g (0.028 mol) of BSA, and 2 ml of methanol were used. The yield of the product was 65.3% and the ratio of the syn-form to the anti-form was 56.5:43.5.

Sources & evidence

ORD record
ord-c59fec548af747fd8a30ff593bc8c95a
Source dataset
uspto-grants-1998_09
Patent number
US05801271

Reaction notes

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