Bromocyclopropane → HCID 86660375, compound

Participants

Reaction Steps

To an argon purged solution of tert-butyl-4-(acetylthio)piperidine-1-carboxylate (51, 1.50 g, 5.86 mmol) in a 5:1 mixture of isopropanol-water (55 mL) was added cyclopropyl bromide (1.52 g, 11.72 mmol) followed by solid LiOH.H2O (1.0 g, 68.67 mmol). The mixture stirred at room temperature and stirred for 16 h and was concentrated under reduced pressure. The residue was dissolved in EtOAc (90 mL) and washed with H2O (25 mL), brine (25 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to give tert-butyl 4-(cyclopropylmethylthio)piperidine-1-carboxylate as a colorless syrup (52, 1.1 g, 69%); 1H NMR (300 MHz, CDCl3) δ 2.98-2.75 (m, 3H), 2.61 (m, 1H), 2.48 (d, J=6.9 Hz, 2H), 2.39-2.28 (m, 1H), 1.74-2.01 (m, 2H), 1.43-1.55 (m, 2H), 1.45 (s, 9H), 1.01-0.88 (m, 1H), 0.52-0.59 (m, 2H), 0.15-0.25 (m, 2H);

Provenance & Evidence