4-Toluenesulfonyl chloride → HCID 69597629, compound

Participants

Reaction Steps

To a solution of (3R,6R)-6-hydroxymethyl-4,4-dimethyl-3-(1-phenyl-ethylamino)-tetrahydro-pyran-2-one (compound of formula XXXIV, 1.42 g, 5.14 mmol) in 45 ml of methylene chloride was added triethylamine (1.1 ml, 7.9 mmol) and p-toluenesulfonyl chloride (1.2 g, 6.2 mmol) at about 0° C. The mixture was warmed to a temperature of about 20° C. to about 25° C. and was stirred for about 46 hours. The mixture was washed twice with water, and the aqueous layers were extracted with methylene chloride. The combined organic layers were dried over MgSO4, filtered and concentrated. Purification of the residue by filtration through a pad of silica gel eluting first with hexane followed by 20% ethyl acetate in hexane afforded 0.4 g of (1R,4R)-8,8-dimethyl-5-(1-phenyl-ethyl)-2-oxa-5-aza-bicyclo[2.2.2]octan-3-one (compound of formula XXXV) as a colorless solid after recrystallization from methanol-water.

Provenance & Evidence