Tetrahydrofuran → HCID 67744901, compound

Participants

Reaction Steps

A stirred mixture of (20S)-4-azido-21-hydroxy-20-methylpregn-4-en-3-one acetate (1.4 g, 3.39 mmole), triphenyl-phosphine (1.08 g), tetrahydrofuran (25 mL) and water (7 mL) was heated at reflux temperature under argon for 18 hours. The solvents were removed from the cooled reaction and the residue was purified by flash chromatography to give (20S)-4-amino-21-hydroxy-20-methylpregn-4-en-3-one acetate (1.1 g, 84%). IR 3470, 3366, 1732, 1674, 1618, 1584, 1254 cm-1 ; MS (CI) 388 (100%, M+1), 328 (70% M+1-AcOH); 1H NMR (CDCl3) δ 0.72 (3H, s, C18 -Me), 1.00 (d, C22 -Me), 1.14 (s, C19 -Me), 2.04 (s, Ac-Me), 3.43 (2H, v br, NH2), 3.76 (1H, dd, 1/2 C21 -CH2), 4.07 (1H, dd, 1/2 C21 -CH2). This compound has the following structure: ##STR5##

Provenance & Evidence