rac-(1R,3S)-3-(methoxycarbonyl)cyclopentane-1-carboxylic acid → rac-methyl (1R,3S)-3-(hydroxymethyl)cyclopentane-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

(1S,3R)-3-(methoxycarbonyl)cyclopentanecarboxylic acid (15.9 gm, 92.3 mmol, 1 equi.) was dissolved in anhydrous THF (250 mL) and cooled down to −78° C. under nitrogen atmosphere. To this was added borane dimethyl sulfide complex (2M solution in THF, 1.66 equi., 147.7 mmol, 74 mL) and stirring was maintained for one hour allowing the temperature to raise to 0° C. temperature and stirred at room temperature for another three hours. The mixture was cooled down to −20° C. and quenched with a slow addition of 1M KH2PO4. Reaction was warmed up to room temperature and stirred for further 20 min and extracted with ether. Organic layer was washed with brine and dried over MgSO4, filtered and concentrated to dryness. The residue was purified by silica gel chromatography with (10% to 80% EtOAc in hexanes) to provide 13 g of (1R,3S)-methyl 3-(hydroxymethyl)cyclopentanecarboxylate 99.

Provenance & Evidence