[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][C:9](=[O:11])[CH2:8][C@H:7]1[C:12]([OH:14])=[O:13])=[O:5])[CH3:2].[BH4-].[Na+].Cl.[Cl-].[Na+]>O1CCCC1>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][CH:9]([OH:11])[CH2:8][C@H:7]1[C:12]([OH:14])=[O:13])=[O:5])[CH3:2]To a cold (ice bath solution of (1R,2R)-4-Oxo-cyclopentane-1,2-dicarboxylic acid monoethyl ester (3.0 g) in tetrahydrofuran (30 mL) was added sodium borohydride (737 mg) in several portions over 5.5 h. After 6.5 h, hydrochloric acid (1N, 40 mL) then sodium chloride (8 g) were added to the reaction mixture. After 30 min, the reaction mixture was extracted with ethyl acetate. The organic layers were dried over sodium sulfate and concentrated in vacuo to afford the title compound (3.2 g, 95%) as colorless oil, used in the next step without further purification. MS (EI): 201.2 (M−H)−.
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