Water → Methyl (2,2-dimethylpent-4-en-1-yl)carbamate

Participants

Reaction Conditions

Reaction Steps

A 1 L round-bottom flask under nitrogen was charged with 2,2-Dimethylpent-4-en-1-amine (9.86 g, 87 mmol), diisopropylethylamine (16.73 ml, 96 mmol), and DCM (100 mL) and cooled to 0° C. A solution of methyl chloroformate (7.08 mL, 91 mmol) in DCM (50 mL) was added dropwise. The reaction mixture was warmed to RT, stirred for 24 hours and poured into water. The mixture was extracted with EtOAc (3×). The combined organic portions were washed with brine, dried with anhydrous MgSO4 and filtered, and the solvent was removed from the filtrate by rotary evaporation. The crude product was purified by silica gel chromatography eluting with 70 hexane/30 EtOAc, to give the title compound. 1H NMR (CDCl3): δ 5.85-5.79 (m, 1H), 5.06-5.02 (m, 2H), 4.46 (s, 1H), 3.67 (s, 3H), 3.02-3.00 (m, 2H), 1.98-1.96 (m, 2H), 0.88 (s, 6H) ppm.

Provenance & Evidence