Ammonia → HCID 90388608, compound

Participants

Reaction Conditions

Reaction Steps

A three-neck flask fitted with a dry ice condenser was cooled to −78° C., and anhydrous ammonia (100 mL) was condensed into the flask. Lithium (0.21 g, 30 mmol) was added, and the resulting blue solution was stirred for 0.5 h. To this was added a solution of compound 36 (820 mg, 3.0 mmol) in dry THF (30 mL). After 3 h, solid NH4Cl was added until the blue color disappeared. The cooling bath was removed and stirring was continued at room temperature overnight. Aqueous NH4Cl was added and the product was extracted into EtOAc (100 mL×3). The combined extracts were washed with brine, dried and the solvent evaporated. Flash column chromatography (silica gel eluted with 10% EtOAc in hexanes) gave compound 37 (615 mg, 75%) as a white solid: [α]D25+52.3 (c 0.13, CHCl3); 1H NMR (CDCl3) δ 3.58 (t, J=7.7 Hz, 1H), 0.68 (s, 3H); 13C NMR (CDCl3) δ 211.7, 81.3, 48.3, 47.8, 45.7, 44.9, 44.5, 43.6, 42.9, 41.0, 37.8, 34.2, 33.7, 30.1, 29.9, 29.0, 25.3, 11.0; IR νmax 3419, 1713 cm−1. Anal. Calcd for (C18H28O2): C, 78.21; H, 10.21. Found: C, 78.29; H, 10.12.

Provenance & Evidence