Hexane → HCID 20664170, compound

Participants

Reaction Steps

Tetrabutylammonium fluoride (3.6 mL, 1N in THF, 3.6 mmol) was added to a solution of dihydro-3-(R)-(3-(R)-((t-butyldimethylsilyloxy)methyl)-4-(S)-(3-fluorophenyl)-pyrrolidin-1-yl)-4,4-dimethyl-2(3H)furanone (500 mg, 1.2 mmol, from Step A) in 1 mL of THF. After 2 h. at room temperature, the solution was diluted with diethyl ether and washed with 1N NaOH and brine. The solution was dried over Na2SO4, filtered and concentrated. Flash chromatography (1:1 hexane:ethyl acetate) provided 203 mg (55% yield) of the title compound. 1H NMR (300 MHz, CDCl3). δ1.17 (s, 3H), 1.22 (s, 3H), 1.80-1.90 (m, 1H), 2.39-2.52 (m, 1H), 3.03-3.20 (m, 5H), 3.25-3.32 (m, 1H), 3.58-3.67 (m, 1H), 3.69-3.78 (m, 1H), 3.88-3.98 (m, 2H), 6.85-6.95 (m, 1H), 7.00-7.10 (m, 2H), 7.21-7.32 (m, 1H). ESI-MS. M/z; (M+H)=308.2.

Provenance & Evidence