Hydrogen Bromide → HCID 21186577, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(4-chlorophenylsulfanyl)-8-(2,2,2-trichloroethoxycarbonyl)-8-azabicyclo-(3.2.1)-octane (8.70 g, 20.28 mmol), 48% HBr (17 mL), and acetic acid (68 mL) was heated to 110° C. for 78 h. The reaction was adjusted to pH 11 by addition of 4 N sodium hydroxide and extracted with methylene chloride. The organic phase was filtered through diatomaceous earth, washed with brine, dried over calcium sulfate and concentrated to afford 3-(4-chlorophenylsulfanyl)-8-azabicyclo-(3.2.1)-octane as a yellow oil. The product was kugelrohr distilled (110-130° C., (pot temperature), 1.5 mm Hg) to give 4.1 g (79%) of 3-(4-chlorophenylsulfanyl)-8-azabicyclo-(3.2.1)-octane as a nearly colorless oil which solidified and had: NMR δ 7.30 (m, 4 H), 3.54 (br t, J=3.5 Hz, 2 H), 3.32 (sym m, 1 H), 1.97-1.72 (m, 5 H), 1.71-1.52 (m, 4 H).

Provenance & Evidence