Nitrogen → HCID 69672148, compound

Participants

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of 2,2-difluoro-1-(pyrrolidin-1-yl)pent-4-en-1-one (260 mg, 1.37 mmol) in dry THF (15 mL) was added BH3-THF (6.6 mL of a 1M solution in THF, 6.60 mmol) at rt. The reaction mixture was stirred at reflux for 18 h, cooled down to rt and concentrated under reduced pressure. The residue was redissolved in MeOH (slow addition) and concentrated under reduced pressure (2×). The resulting oil was then redissolved in THF (5 mL), treated with aq. 2N NaOH (0.8 mL) and aq. 30% H2O2 (0.8 mL). The mixture was stirred at rt for 2 h. Water was then added, the layers separated and the aq. layer extracted with EA. The combined org. extracts were washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The crude residue was purified by FC (hept-EA, 1:1→3:7) to give 4,4-difluoro-5-(pyrrolidin-1-yl)pentan-2-ol as a colorless oil and 4,4-difluoro-5-(pyrrolidin-1-yl)pentan-1-ol as a yellow oil. LC-MS-conditions 08: tR=0.38 min; [M+H]+=194.39 and tR=0.51 min; [M+H]+=194.38.

Provenance & Evidence