3-Bromo-1-propanol → HCID 57941457, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (4S,7R)-2-(2,4-difluoro-phenyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 14; 355 mg, 1.17 mmol), tetrabutylammonium iodide (220 mg, 0.60 mmol) and 3-bromo-1-propanol (450 μL, 5.0 mmol) in dimethylformamide (4 mL) was heated at 100° C. for 21 h. Dichloromethane (100 mL), and the solution was washed with aqueous sodium thiosulfate (25 mL), and water (4×25 mL). The solution was dried (magnesium sulfate), and filtered. Silica gel was added and the solvent was evaporated. The resulting material was purified using an ISCO 12 g column, eluting with 0-5% methanol/ethyl acetate. Fractions containing the product were combined, evaporated, and dried under high vacuum at 95° C. overnight to give a gum that solidified on scratching. In this way was obtained (4S,7R)-2-(2,4-difluoro-phenyl)-1-(3-hydroxy-propyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (21 mg, 9%) as a light brown solid. APCI(+)-MS (M+H) 363.

Provenance & Evidence