Allyl bromide → Tert-butyl 4-((allyloxy)methyl)-4-methylpiperidine-1-carboxylate

Participants

Reaction Steps

To a solution of e tert-butyl 4-(hydroxymethyl)-4-methylpiperidine-1-carboxylate (479 mg, 2.089 mmol) in DMA (3 mL) was added 60 wt % sodium hydride (125 mg, 3.13 mmol). Reaction immediately turned yellow. Stirred for 5 min and added 3-bromoprop-1-ene (1263 mg, 10.44 mmol). After 3 h, partitioned between EtOAc and sat.aq.NH4Cl. The organic phase was washed with water (3×), brine and dried (MgSO4), filtered, and concentrated to give 471 mg (75%) of tert-butyl 4-((allyloxy)methyl)-4-methylpiperidine-1-carboxylate as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 5.91 (ddt, J=17.2, 10.5, 5.3 Hz, 1H), 5.29 (dq, J=17.1, 1.7 Hz, 1H), 5.19 (dq, J=10.4, 1.5 Hz, 1H), 3.98 (dt, J=5.3, 1.5 Hz, 2H), 3.62 (br. s., 2H), 3.23-3.14 (m, 4H), 1.56-1.49 (m, 2H), 1.48 (s, 9H), 1.37-1.28 (m, 2H), 1.02 (s, 3H). LCMS (M+1)=270.25.

Provenance & Evidence