N-Methylethylamine → HCID 60134452, compound

Participants

Reaction Steps

To a stirred ice cold solution of N-methylethanamine (2.65 mL, 1 equiv, 30.9 mmol) and DIEA (7.0 mL, 1.3 equiv, 40.2 mmol) in anhydrous DCM (150 mL) was added 3-azido-3-methylbutanoyl chloride (5.0 g, 30.9 mmol) in small portions. The ice bath was removed and the reaction was stirred and left at room temperature for 3 h. The contents of the reaction were poured into a separatory funnel. The organic layer was washed with 1 M HCl (3×100 mL) and saturated NaHCO3 (2×100 mL). It was dried over anhydrous MgSO4, filtered, concentrated and dried under high vacuum to give a crude oil (7.14 g, 96.1%). This material was purified on an ISCO flash chromatography system with ethyl acetate and hexanes as eluent. The desired fractions were collected and concentrated to give a pale yellow oil (5.09 g, 89.4%). 1H NMR (CDCl3, 400 MHz): δ 1.42 (s, 6H), 2.40 (s, 2H), (dq, J=2.4 & 8.8, 2H). LRMS (ESI+) for C8H16N4O (184.1); Found: 185 (MH+).

Provenance & Evidence