Formic Acid → ethyl (3R)-2-chloro-3-hydroxy-4-phenylbutyrate

HRID 1173771

Reaction equation

[Cl:1][CH:2]([C:8](=[O:16])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].CC1C=CC(C(C)C)=CC=1.C(N(CC)CC)C.C(O)=O>ClC1C=CC=CC=1.C(OCC)(=O)C.O>[Cl:1][CH:2]([C@H:8]([OH:16])[CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

Conditions

Temperature: 40 °C

Procedure

Ethyl 2-chloro-3-oxo-4-phenylbutyrate (180 mg, 0.7 mmol) and RuCl[(S,S)-TsDPEN])p-cymene) complex (10 mg, 2 mol %) were mixed, and the mixture was dissolved in chlorobenzene (1 ml). A chlorobenzene solution (1 ml) of triethylamine (374 mg, 5 equivalents) was added, and then a chlorobenzene solution (1 ml) of formic acid (102 mg, 3 equivalents) was gradually added dropwise. After the mixture was stirred at 40° C. for 3 hours, water (4 ml) was added. Ethyl acetate (10 ml) was added for extraction, and the organic layer was concentrated under reduced pressure to obtain the title compound as a brown oil (182 mg, yield: 100%).

Workup

concentrationthe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record: ord-0fb06840647044cc93f881a40e5455f8
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834190B2

Linked notes

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