Cyclobutanone → HCID 46855230, compound

Participants

Reaction Steps

A solution of cyclobutanone (137 mL, 1.83 mol) and (2R,4R)1-[2-([1,4]diazepane-1-carbonyl)-4-hydroxy-pyrrolidin-1-yl]-ethanone (358 g, 1.4 mol) in dichloroethane (3.7 L) was stirred for 1 h at rt. Sodium triacetoxyborohydride (422.4 g, 1.99 mol) was then added in 4 portions over 2 h. The mixture was stirred for 14 h and then NaOH(aq) (50 wt %, 210 mL) was added. The mixture was stirred for 2 h and then MgSO4 (264 g) was added. After an additional 1.5 h of stirring, the mixture was filtered and then concentrated. Purification by FCC (5% 2 M NH3 in MeOH/95% CH2Cl2) provided the title compound as an oil (277 g, 64%). MS (ESI): mass calcd. for C16H27N3O3, 309.2; m/z found, 310.2 [M+H]+. 1H NMR (CDCl3): 6.11-6.04 (m, 1H), 4.93-4.70 (m, 1H), 4.46-4.34 (m, 1H), 3.96-3.44 (m, 6H), 2.96-2.83 (m, 1H), 2.76-2.37 (m, 4H), 2.30-2.20 (m 1H), 2.10-1.55 (m, 12H).

Provenance & Evidence