Water → Tert-butyl 4-(methylthio)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

tert-Butyl 4-[(methylsulfonyl)oxy]piperidine-1-carboxylate 5-2 (27.060 g, 96.87 mmol) was dissolved in 150 mL DMF (dimethylformamide). Sodium thiomethoxide (13.579 g, 193.73 mmol) was added and the solution was heated to 80° C. for 17 hours. The solution was allowed to cool to room temperture. The reaction was then poured into 200 mL H2O and was extracted with ether (4×). The combined organic layers were dried (Na2SO4), filtered, and concentrated to afford tert-butyl 4-(methylthio)piperidine-1-carboxylate 5-3 as a yellow oil. 1H NMR (CDCl3) δ 4.01 (bs, 2H), 3.92 (m, 1H), 3.49 (m, 1H), 2.89 (m, 2H), 2.67 (m, 1H), 2.10 (s, 3H), 1.95-1.89 (m, 2H), 1.46 (s, 9H).

Provenance & Evidence