HCID 14980114, compound → HCID 69208040, compound

Participants

Reaction Steps

Representative preparation of 3-formamide estrane derivatives: Preparation of 3-formamide-17-methylene-2-methoxyestra-1,3,5(10)-triene (Compound #88): 3-Amino-17-methylene-2-methoxyestra-1,3,5(10)-triene (293 mg, 0.99 mmol) was dissolved in chloroform (1 mL) and trimethylacetyl formic anhydride (170 mg, 1.30 mmol, prepared as in Vlietstra et al Recueil, 1982, 101, 460) was added. The mixture was stirred 40 min, after which, the solvent was removed under reduced pressure. The product was purified by titurating with hexanes and isolating the precipitate by decanting after the precipitate was centrifuged. Obtain 150 mg white powder (0.417 mmol, 42% yield). 1H NMR (300 MHz, CD3OD) δ 8.27 (s, 1H), 7.88 (s, 1H), 6.94 (s, 1H), 4.72-4.67 (m, 2H), 3.88 (s, rotamer 1) and 3.86 (s, rotamer 2, total 3H), 2.87-2.76 (m, 2H), 2.66-1.19 (m, 13H), 0.87 (s, 3H).

Provenance & Evidence