Dimethyl Sulfoxide → HCID 56629887, compound

A mixture of 190 mg of (1S,3RS)-1-butyl-3-(p-toluene-sulphonyloxy)cyclopentane (prepared in Reference Example 12), 150 mg of sodium cyanide and 1.5 ml of anhydrous dimethyl sulphoxide was stirred for 30 mins. at 50° C. After diluting with 3 ml of water, the mixture was extracted with 10 ml of a mixture of pentane and diethyl ether (1:1). The extract was washed with water and a saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulphate, and concentrated under ambient pressure at 50° C. The residue was purified by column chromatography on silica gel using a mixture of hexane and ethyl acetate (1:3) as eluent to give 73 mg of the title compound having the following physical characteristics.

1. customat 50° C
2. extractionthe mixture was extracted with 10 ml of a mixture of pentane and diethyl ether (1:1)
3. washThe extract was washed with water
4. dry with materiala saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulphate
5. concentrationconcentrated under ambient pressure at 50° C
6. customThe residue was purified by column chromatography on silica gel using
7. additiona mixture of hexane and ethyl acetate (1:3) as eluent

ORD record

ord-0f05e5f5c17e4066adc901fcc42c8a4d

Source dataset

uspto-grants-1985_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04562207