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 tetrahydrofuran (30 ml) at -30° C. and the reaction mixture stirred for 2 hours. A solution of 1-azabicyclo[3.2.1]octan-6-one (1.1 g, 8.8 mmol) in tetrahydrofuran (10 ml) was added dropwise and the reaction mixture allowed to warm to room temperature. Water (20 ml) was added and extracted (3×) with dichloromethane. The combined extracts were dried (MgSO4) and concentrated and the residue purified by chromatography on alumina eluting with dichloromethane/methanol (97:3) to give the title compound as a colourless oil (2 g); m/e 227 (M+); δ (360 MHz, CDCl3) 1.23-1.38 and 1.56-1.86 (1H and 3H respectively, each m, 3CH2 and 4CH2 ), 2.08-2.24 (2H, m, SCH2CH2), 2.76-3.00 (9H, m, 2×SCH2, 2CH2, 5CH and 8CH2), 3.42 (1H, d, J=17 Hz, one of 7CH2) and 3.56 (1H, d, J=17 Hz, one of 7CH2).

Provenance & Evidence