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

HRID 575988Notes

Reaction equation

HRID 575988 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-83301f5eb5614c7d87580dcdd0d9b076
Source dataset
uspto-grants-2015_05
Patent number
US09035073B2

Reaction notes

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