Ammonia → HCID 22800292, compound

Participants

Reaction Steps

N-Methyl morpholine (6.0 ml) was added to a solution of N-t-butoxy-carbonyl-trans-3-methyl-L-proline (1.1 g) in tetrahydrofuran (50 ml) at -20°. Freshly distilled isobutylchloroformate (0.8 g) was added dropwise and the solution stirred for 10 minutes at -20°. Concentrated ammonia solution (5 ml) was added and the solution stirred for 2 hours, evaporated, the residue taken up in ethyl acetate (100 ml) and the solution washed with 10% aqueous sodium bicarbonate, brine and dried (Na2SO4). Evaporation gave the crude crystalline product (1.0 g). Recrystallisation from ethyl acetate/light petroleum (40°-60°) gave the desired product (0.91 g) m.p. 100°-101°, [α]D20 -79.7° (c, 1.0, chloroform)

Provenance & Evidence