Dichloromethane → (1R,2S)-3-oxo-2-pentyl-cyclopentaneacetic acid

Reaction equation

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

Participants

Procedure

Into a Schlenk type vessel, kept anhydrous and under Ar, there was injected the precatalytic solution (6.75 ml) containing 47 mg (0.05 mmole) of bis(trifluoro-acetato)[(+)-(R)-2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl]ruthenium (II), 3-oxo-2-pentyl-1-cyclopentene-1-acetic acid (0.5 g, 2.4 mmole), CH2Cl2 (5 ml), methanol (5 ml) and triethylamine (10.28 mg, 0.1 mmole, 14 μl, dist. over KOH). After stirring for 5 min, the orange soltion was filtered through a single use filter (Acrodisc 0.45 μm) in a dry autoclave (100 ml/107Pa) under Ar. The autoclave was then connected to a source of hydrogen and rinsed 5× with hydrogen at a pressure of 106Pa. The autoclave was then pressurized at 9×106Pa. Stirring at this pressure and 25° was carried out during 120 h. Afterwards, the pressure was gently released, the autoclave opened and the orange solution concentrated.