Benzyl Bromide → 1-Benzyl-3-(3,4-difluorophenyl)-3-methoxypyrrolidine

HRID 1188201Notes

Reaction equation

HRID 1188201 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2([O:14][CH3:15])[CH2:13][CH2:12][NH:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[H-].[Na+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O>[CH2:18]([N:11]1[CH2:12][CH2:13][C:9]([C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=2)([O:14][CH3:15])[CH2:10]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 462192213-(3,4-Difluorophenyl)-3-methoxypyrrolidine

Product 1

HCID 674032321-Benzyl-3-(3,4-difluorophenyl)-3-methoxypyrrolidineYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Preparation according to Preparation 14. 3-(3,4-Difluorophenyl)-3-methoxypyrrolidine (1.15 g, 5.4 mmol), dry dimethyl formamide (5 mL), sodium hydride (60% dispersion in mineral oil, 0.259 g, 6.48 mmol). Benzylbromide (0.642 mL, 5.4 mmol) in dry dimethyl formamide (5 mL). Work up according to Preparation 14. Purification by flash column chromatography on silica gel (ethyl acetate) gave the title compound (0.9 g, 55%). MS m/z (rel. intensity, 70 eV) 288 (12), 273 (14), 133 (53), 132 (30), 91 (bp).

Workup

  1. customPreparation
  2. customaccording to Preparation 14
  3. customWork up according to Preparation 14
  4. customPurification by flash column chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-0967946f2a8b4f68870e56e3cd983714
Source dataset
uspto-grants-2014_03
Patent number
US08673962B2

Reaction notes

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