Methylamine → HCID 69419650, compound

Participants

Reaction Conditions

Reaction Steps

Methylamine (2.0M in THF; 40 ml, 80 mmol) was added dropwise over 5 minutes to a solution of 2-cyclopenten-1-one (6.8 ml, 81 mmol) in dichloromethane (70 ml) cooled to −4° C. The resulting mixture was stirred at −4° C. to +1° C. for 1 h 30 min. then treated with di-tert-butyl dicarbonate (17.81 g, 81.6 mmol) in dichloromethane (25 ml). The reaction mixture was stirred at 0° C. for 15 min., allowed to warm to room temperature over 30 min. then stirred overnight (20 h). The mixture was concentrated in vacuo and the residue purified by flash chromatography, eluting with 1:3 then 1:2 ethyl acetate-isohexane, to give the title compound (7.78 g, 45%) as an pale amber oil; δH (400 MHz, CDCl3) 1.47 (9H, s), 1.93-2.04 (1H, m), 2.14-2.31 (3H, m), 2.37-2.47 (2H, m), 2.80 (3H, s), 4.71 (1H, br s).

Provenance & Evidence