Water → HCID 10427683, compound

Participants

Reaction Steps

To a stirred solution of (20S)-4-azido-21-hydroxy-20-methylpregn-4-en-3-one (3.15 mmole) in tetrahydrofuran (20 mL)-water (7 mL) was added triphenylphosphine (1.41 g, 5.38 mmole). The reaction was heated at reflux temperature for 16 hours. Most of the tetrahydrofuran was removed under vacuum. Dichloromethane was added to the mixture and the organic solution was placed atop a column of silica gel and flash chromatographed (hexane-30% ethyl acetate). The fractions containing the product were combined and concentrated to a white solid which was crystallized from diethyl ether to give (20S)-4-amino-21-hydroxy-20-methylpregn-4-en-3-one. IR 3510, 3470, 3384, 1648, 1614, 1576 cm-1 ; MS (CI) 346 (100%, M+ +1) (EI) 345 (65%, M+), 302 (100%); 1H NMR δ (CDCl3) 0.73 (3H, s, C18 -Me), 1.04 (d, C21 -Me), 1.15 (s, C19 -Me), 2.42-2.56 (3H m) 3.73 (v br NH2) 3.36 (1H dd 1/2 C21 -CH2), 3.63 (1H, dd, 1/2 C21 -CH2); 13C NMR δ (CDCl3) 132.85, 139.15, 194.38. This compound has the following structure: ##STR4##

Provenance & Evidence