Methanol → HCID 22853247, compound

Participants

Reaction Conditions

Reaction Steps

A 4.9 g (24.37 mmol) sample of 1-BOC-azetidine-2-carboxylic acid, from step a above, was dissolved in 35 mL of THF, and stirred under N2 at -10° C. To this solution was added 2.68 mL of NMM, and the mixture was stirred for 5 min. Next was added 3.16 mL (24.37 mmol) of isobutyl chloroformate, and the reaction was stirred for 20 min. To the reaction was next added 0.99 mL of methanol, and the stirred mixture was warmed to room temperature and stirred for 16 hr. The reaction was adjusted to an acidic pH and extracted with ethyl acetate. The solvent was removed, and the residue was purified on silica gel, eluting with 2:1 hexane:ethyl acetate to give 2.00 g of the title product. MS: 177 (M-C4H8 +NH4)+, 216 (M+H)+, 233 (M+NH4)+. 1H NMR (CDCl3) δ: 1.42 (s, 9H), 2.15-2.25 (m, 1H), 2.45-2.55 (m, 1H), 3.78 (s, 3H), 3.85-3.95 (m, 1H), 4.00-4.10 (m, 1H), 4.61 (dd, 1H, J=5, 10 Hz).

Provenance & Evidence