Iodoethane → 3-(3,4-Difluorophenyl)-1-ethyl-3-methoxypyrrolidine

HRID 1188167Notes

Reaction equation

HRID 1188167 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].[CH2:16](N(CC)CC)[CH3:17].ICC>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([C:9]2([O:14][CH3:15])[CH2:13][CH2:12][N:11]([CH2:16][CH3:17])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 8471TriethylamineHCID 462192213-(3,4-Difluorophenyl)-3-methoxypyrrolidine

Product 1

HCID 462192223-(3,4-Difluorophenyl)-1-ethyl-3-methoxypyrrolidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (−)-3-(3,4-difluorophenyl)-3-methoxypyrrolidine (0.013 g, 0.061 mmol) and triethylamine (17.1 μL, 0.122 mmol) in tetrahydrofuran (2 ml), was added iodoethane (7.3 μL, 0.091 mmol), the resulting solution was stirred at ambient temperature for 24 h. The crude mixture was purified on a Biotage Isolute SCX-3 SPE column (washed with methanol and eluted with methanol/triethylamine, 4:1). The solvent was evaporated and the crude product was analyzed by GCMS. Analysis showed 76% conversion. MS m/z (relative intensity, 70 eV) 241 (M+, 7), 226 (57), 211 (24), 141 (43), 71 (bp).

Workup

  1. customThe crude mixture was purified on a Biotage Isolute SCX-3 SPE column (washed with methanol and eluted with methanol/triethylamine, 4:1)
  2. customThe solvent was evaporated

Sources & evidence

ORD record
ord-40ec3ba7a9ed4002b1ae749c21a46742
Source dataset
uspto-grants-2014_03
Patent number
US08673962B2

Reaction notes

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