Dichloromethane → methyl (2R, 3S)-2-(N-benzoylamino)methyl-3-hydroxybutanoate

HRID 703279

Reaction equation

C(Cl)Cl.[C:4]([NH:12][CH2:13][CH:14]([C:19](=[O:21])[CH3:20])[C:15]([O:17][CH3:18])=[O:16])(=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CCN(CC)CC>[C:4]([NH:12][CH2:13][C@H:14]([C@@H:19]([OH:21])[CH3:20])[C:15]([O:17][CH3:18])=[O:16])(=[O:11])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 45 °C

Procedure

In a 100 ml-volume autoclave whose atmosphere had been displaced with nitrogen was added a methylene chloride solution of 2.5 g of methyl 2-(N-benzoylamino)methyl-3-oxobutanoate and 84.5 mg (0.05 mmole) of Ru2Cl4 ((-)-BINAP2 (NEt3), and a reaction was conducted by stirring at 45° C. under a hydrogen pressure of 70 kg/cm2 for 24 hours. The reaction mixture was taken out, and the solvent was removed by distillation under reduced pressure of 20 mmHg at 30° C. The residue was purified by silica gel column chromatography using a 7/3 (by volume) mixture of hexane and isopropanol as an eluent to obtain 2.27 g (yield: 91%) of methyl (2R, 3S)-2-(N-benzoylamino)methyl-3-hydroxybutanoate having an optical purity of 97 %ee.

Workup

customthe solvent was removed by distillation under reduced pressure of 20 mmHg at 30° C
customThe residue was purified by silica gel column chromatography
additiona 7/3 (by volume) mixture of hexane and isopropanol as an eluent

Sources & evidence

ORD record: ord-40ea430dc7dc49dbb7f8848a2d950e32
Source dataset: uspto-grants-1991_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04981992

Linked notes

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