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

Temperature

80 °C

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.

1. customThe reaction mixture was then quenched by the addition of 30 mL of water after it
2. temperaturewas cooled to room temperature with a water bath
3. extractionThe solution was extracted with 3×30 mL of ether
4. washThe combined organic layer was washed with 2×50 mL of brine
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated under vacuum

ORD record

ord-9dd493a0d53a4e358bd3b7db4691ec98

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09296732B2