Sodium borohydride → 1-(5-Hydroxymethylthiophen-2-yl)-cyclopent-3ene carboxylic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:11]2[S:12][C:13]([CH:16]=[O:17])=[CH:14][CH:15]=2)[CH2:10][CH:9]=[CH:8][CH2:7]1)=[O:5])[CH3:2].[BH4-].[Na+]>CO>[CH2:1]([O:3][C:4]([C:6]1([C:11]2[S:12][C:13]([CH2:16][OH:17])=[CH:14][CH:15]=2)[CH2:7][CH:8]=[CH:9][CH2:10]1)=[O:5])[CH3:2]Participants
4
Procedure
To a solution of the product of Step 2, above (3) (0.93 mmol), in 3 ml methanol at 0° C. was added sodium borohydride (2.0 mmol). The reaction was slowly allowed to warm to ambient temperature and was stirred for 2 hours. The reaction was quenched with saturated ammonium chloride and extracted (2×10 ml EtOAc). The organic extracts were combined and washed with saturated sodium bicarbonate and brine, dried with MgSO4, filtered and concentrated to yield the title compound (4).