(Diethylamino)sulfur trifluoride → HCID 68158539, compound

Temperature

-70 °C

Intermediate IV-2: A solution of (3aS,6aS)-rel-1-(3a,4,6,6a-tetrahydro-furo[3,4-d]isoxazol-3-yl)-methanol (14.0 mmol) in dichloromethane (40 ml) was treated dropwise with a solution of (diethylamino)sulfur trifluoride (15.4 mmol) in dichloromethane (5 ml) at −70° C. The colorless turbid solution was stirred at −70° C. for 30 minutes and then allowed to warm to room temperature while its color turned to brown. After stirring for one hour the dark brown solution was cooled in an ice-bath and quenched with a saturated solution of sodium hydrogencarbonate (50 ml). The aqueous layer was separated and extracted twice with dichloromethane. The combined organic layers were dried over sodium sulphate, then evaporated. The crude product was purified by chromatography on silica gel using a gradient of heptane and ethyl acetate=100:0 to 80:20 as the eluent. The (3aS,6aS)-rel-3-fluoromethyl-3a,4,6,6a-tetrahydro-furo[3,4-d]isoxazole (814 mg, 40% yield) was obtained as a light yellow solid. MS: m/z=146.2 [M+H]+.

1. temperatureto warm to room temperature while its color
2. stirringAfter stirring for one hour the dark brown solution
3. temperaturewas cooled in an ice-bath
4. customquenched with a saturated solution of sodium hydrogencarbonate (50 ml)
5. customThe aqueous layer was separated
6. extractionextracted twice with dichloromethane
7. dry with materialThe combined organic layers were dried over sodium sulphate
8. customevaporated
9. customThe crude product was purified by chromatography on silica gel using a gradient of heptane and ethyl acetate=100:0 to 80:20 as the eluent

ORD record

ord-4e4b3d9ebd6641d980eba127f3013c33

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08404680B2