4-Toluenesulfonyl chloride → HCID 69597629, compound

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.

1. temperatureThe mixture was warmed to a temperature of about 20° C. to about 25° C.
2. washThe mixture was washed twice with water
3. extractionthe aqueous layers were extracted with methylene chloride
4. dry with materialThe combined organic layers were dried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated
7. customPurification of the residue
8. filtrationby filtration through a pad of silica gel eluting first with hexane

ORD record

ord-f1e3ae1e48fd426a9fd19bf75211ee5a

Source dataset

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07030242B2