Ethyl bromoacetate → N-2-Propen-1-ylglycine ethyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl bromoacetate 52 (3 g, 18.0 mmol) in dry tetrahydrofuran (20 cm3) was added dropwise to an ice-cold solution of allylamine 53 (2.05 g, 36 mmol) in dry tetrahydrofuran (20 cm3) over 3 min. The solution was stirred at 0° C. for 2.5 h (a white precipitate was observed after 2 h), concentrated in vacuo and suspended in diethyl ether. The white suspension was filtered through Celite™ and the solvent removed to yield the crude product which was purified by chromatography (silica gel, 1:1, hexane:ethyl acetate) to give alkene 54 (1.209 g, 47%) as a light yellow oil: δH (300 MHz; CDCl3; Me4Si) 1.17 (3H, t, J 7.1, OCH2CH3), 1.70 (1H, br s, N—H), 3.16 [211, d, J 5.9, CH2(allyl)], 3.28 (2H, s, CH2Gly), 4.08 (2H, q, J 7.1, OCH2CH3), 4.98-5.12 (2H, m, ═CH2) and 5.70-5.85 (1H, m, C(H)═CH2); δC (75 MHz; CDCl3) 13.9 (CH3, OCH2CH3), 49.7 (CH2), 51.6 (CH2), 60.4 (CH2, OCH2CH3), 116.2 (CH2, ═CH2), 135.9 (CH, C(H)═CH2) and 172.2 (quat., CO).

Provenance & Evidence