1-Bromopropane → HCID 69676465, compound

Participants

Reaction Steps

A solution of (S)-tert-butyl 3-aminopiperidine-1-carboxylate (500 mg, 2.49 mmol) and 1-bromopropane (335 mg, 2.74 mmol) and DIEA (0.11 mL, 6.24 mmol) in DMF (4 mL) was heated at 100° C. for overnight. After reaction was shown to be complete as indicated by TLC, the mixture was diluted with EtOAc (30 mL) and washed with water (2×15 mL). The organic layer was separated, dried over Na2SO4, concentrated in vacuo to afford a residue which was purified by column chromatography (silica gel, gradient MeOH in CH2Cl2) to yield the titled intermediate (605 mg, 57%). 1H NMR (400 MHz, DMSO-d6): δ 3.89-3.64 (m, 3H), 2.80-2.66 (m, 2H), 2.50-2.35 (m, 3H), 1.89-1.83 (m, 2H), 1.61-1.58 (m, 2H), 1.38 (s, 9H), 1.35-1.29 9m, 2H), 0.82 (t, J=7.2 Hz, 3H). ES-MS: m/z [M+1]=243.

Provenance & Evidence