2-(4-Bromophenoxy)-2-methyl-1-(pyrrolidin-1-yl)propan-1-one → 1-(2-(4-Bromophenoxy)-2-methylpropyl)pyrrolidine
Reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]([CH3:16])([CH3:15])[C:8]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=O)=[CH:4][CH:3]=1>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]([CH3:16])([CH3:15])[CH2:8][N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:17][CH:18]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
BH3×THF (1M, 27.0 mmol, 27.0 mL) was added dropwise under argon to 2-(4-bromophenoxy)-2-methyl-1-(pyrrolidin-1-yl)propan-1-one (2.12 g, 6.8 mmol; see step (a)) in THF (40 mL) at 0° C. The reaction was quenched by careful addition of NH4Cl (aq. sat.). The reaction mixture was acidified by HCl (1M). NaOH (aq. 0.5M, 30 mL) was added to the filtrate which was then extracted with CH2Cl2. The combined extracts were washed with brine, dried (Na2SO4), concentrated and distilled under reduced pressure to yield the title compound (1.5 g, 76%).