Water → HCID 21476660, compound

Participants

Reaction Steps

n-Butyl lithium (6.05 ml of a 1.6M solution in hexane, 9.7 mmol) was added dropwise to a solution of 2-trimethylsilyl-1,3-dithiane (1.86 g, 9.7 mmol), in THF (30 ml) at -30° C. and the reaction mixture stirred for 2 hr. A solution of 1-azabicyclo [3.2.1]octan-6-one (1.1 g, 8.8 mmol) in THF (10 ml) was added dropwise and the reaction mixture allowed to warm to room temperature. Water (20 ml) was added and extracted (3×50 ml) with dichloromethane. The combined extracts were dried (MgSO4) and evaporated and the residue chromatographed through alumina eluting with dichloromethane/methanol (97:3) to afford the title compound as a clear liquid, (2 g), m/e 227 (M+); δ(60 MHz; CDCl3) 1.10-2.90 (15H, m, 7×CH2 and CH); 3.38 (2H, AB q, J=17 Hz, CH2 --C=C).

Provenance & Evidence