Trimethylaluminum → HCID 70654405, compound

Participants

Reaction Conditions

Reaction Steps

A solution of the {rel-(3R,4S)-4-[(S)-1-amino-1-(2-fluoro-phenyl)-ethyl]-tetrahydro-furan-3-ylsulfanyl}-acetonitrile (460 mg, 1.64 mmol) in toluene (6 ml) was treated dropwise with trimethylaluminum (902 μl, 1.8 mmol) at room temperature. The reaction mixture was stirred at 60° C. for 2 hours, thereafter, extracted with a mixture of a saturated solution of sodium hydrogencarbonate and ethyl acetate. The combined organic layers were dried over sodium sulphate and evaporated at reduced pressure. The residue was purified by flash chromatography on silica gel using a mixture of ethyl acetate, methanol, ammonium hydroxide=100:10:1 as the eluent. The (3aR,8S,8aS)-rel-8-(2-fluoro-phenyl)-8-methyl-1,3,3a,5,8,8a-hexahydro-2-oxa-4-thia-7-aza-azulen-6-ylamine (200 mg, 43% yield) was obtained as a light yellow oil. MS (ISP): m/z=281.0 [M+H]+.

Provenance & Evidence