Sodium borohydride → tert-Butyl 4-sulfanylpiperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of crude tert-butyl 4-thioxopiperidine-1-carboxylate (2 g, 9.30 mmol, 1.00 equiv) in ethanol (20 mL) contained in a 100-mL 3-necked round-bottom flask under nitrogen was added sodium borohydride (570 mg, 15.00 mmol, 1.50 equiv) in several portions. The resulting solution was stirred at 80° C. for 2 h. The reaction mixture was then quenched by the addition of 30 mL of water after it was cooled to room temperature with a water bath. The solution was extracted with 3×30 mL of ether and the organic layers combined. The combined organic layer was washed with 2×50 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to give 2.34 g of crude tert-butyl 4-mercaptopiperidine-1-carboxylate as yellow oil.

Provenance & Evidence