2-(4-Bromophenoxy)-2-methyl-1-(pyrrolidin-1-yl)propan-1-one → 1-(2-(4-Bromophenoxy)-2-methylpropyl)pyrrolidine

HRID 646125Notes

Reaction equation

HRID 646125 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]=1

Participants

3

Reactant 1

HCID 686947812-(4-Bromophenoxy)-2-methyl-1-(pyrrolidin-1-yl)propan-1-one

Product 1

HCID 686966861-(2-(4-Bromophenoxy)-2-methylpropyl)pyrrolidineYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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%).

Workup

  1. customThe reaction was quenched by careful addition of NH4Cl (aq. sat.)
  2. additionNaOH (aq. 0.5M, 30 mL) was added to the filtrate which
  3. extractionwas then extracted with CH2Cl2
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-93d0b71ad2134347ac60b247fbac09b3
Source dataset
uspto-grants-2010_04
Patent number
US07705023B2

Reaction notes

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