Dichloromethane → Estra-1,3,5(10)-trien-17-ol, 4-amino-, (17β)-

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Reaction Steps

A solution of 4-nitroestra-1,3,5(10)-trien-3,17-diol 3-O-triflate (2.13 g, 4.74 mmol) in 100 ml of methanol containing triethylamine (6.60 , 4.8 mmol) and 10% Pd/C (430 mg. 20% by weight) was hydrogenated in a Parr apparatus at 16 psi for 5 hr. TLC using 95% dichlormethane 1% methanol showed one major product and 3 minor constituents. The reaction mixture was filtered through Celite and the filtrate was evaporated to dryness. The residue was dissolved in excess dichloromethane and the solution was washed with water. The extract was dried over sodium sulfate and filtered. The filtrate was evaporated to dryness. The residue crystallized from methanol as a cluster of colorless needles of 4-aminoestra-1,3,5(10)-trien-17β-ol; wt. 320 mg. (25% yield), mp 189°-192° C. Mass Spectrum: m/z 271 (M+), 237 (M--H2O+NH2). 1H NMR 7.23-6.51 (m, 3, H1, H2, H3 aromatic) 3.71-3.45 (t, 1, 17H), 2.57-1.23 (m, 18), 0.876 (s, 3, C18CH3).

Provenance & Evidence