Water → HCID 67744913, compound

Participants

Reaction Steps

To a vigorously stirred solution of the (20S)-4,5-epoxy-21-hydroxy-20-methylpregnan-3-one acetate (2.0 g, 5.15 mmole) obtained in Example 7, in dimethyl sulfoxide (70 mL) and heated to 60° C., there was added sodium azide (5.4 g) and then concentrated sulfuric acid (0.37 mL). The mixture was quickly brought to a temperature of 100° C. and held at that temperature for 1 hour. The cooled mixture was then poured into cold water (450 mL). The solids were collected by filtration, washed with water, and dried by suction to give a yellow solid which was purified by flash chromatography to give (20S)-4-amino-21-hydroxy-20-methylpregna-4,6-dien-3-one acetate (1.04 g, 52.5%). IR 3488, 3446, 3360, 1740, 1668, 1612 (m), 1592 (m), 1562 (m), 1252 cm-1 ; MS (CI) 386 (20%, M +1), 326 (100%, M+1 - AcOH); 1H NMR (CDCl3) δ 0.78 (3H, s, C18 -Me), 1.03 (d, C22 -Me), 1.06 (s, C19 -Me), 2.07 (s, Ac-Me), 3.69+3.78 (3H, v br+dd, NH2 1/2 C21 -CH2), 4.09 (1H, dd, 1/2 C21 -CH2), 5.97 (1H, dd), 6.30 (1H, dd). This compound has the following structure: ##STR5##

Provenance & Evidence