Hydrochloric Acid → HCID 90388597, compound

Participants

Reaction Steps

To a solution of compound 54 (110 mg, 0.4 mmol) in THF (10 mL) was added LiAl(OtBu)3H at 40° C. After 2 h, 3 N HCl, was added and the product extracted into EtOAc (50 mL×3). The combined extracts were dried, filtered and concentrated. The residue was purified by flash column chromatography (silica gel eluted with 25% EtOAc in hexanes) to give compound 55 (4aR separated from 4aS diastereomer, 65 mg, 56% from compound 36) as a white solid: mp 174-176° C.; [α]D25 −36.2 (c 0.21, CHCl3); 1H NMR (CDCl3) δ 3.65-3.55 (m, 1H), 0.82 (s, 3H); 13C NMR (CDCl3) δ 221.1, 71.4, 47.9, 45.7, 40.1, 39.1, 38.8, 38.4, 36.2, 35.6, 35.5, 31.7, 29.6, 29.3, 28.4, 25.5, 24.0, 13.5; IR νmax 3460, 1738 cm−1. Anal. Calcd for (C18H28O2): C, 78.21; H, 10.21. Found: C, 78.37; H, 10.20.

Provenance & Evidence