Iodoethane → 3-(3,5-Difluorophenyl)-1-ethyl-3-methoxypyrrolidine

HRID 1188163Notes

Reaction equation

HRID 1188163 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]=[C:6]([F:8])[CH:7]=1.[CH2:16](N(CC)CC)[CH3:17].ICC>O1CCCC1.CO>[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]=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 8471TriethylamineHCID 199358743-(3,5-Difluorophenyl)-3-methoxypyrrolidine

Product 1

HCID 462192253-(3,5-Difluorophenyl)-1-ethyl-3-methoxypyrrolidine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (+)-3-(3,5-difluorophenyl)-3-methoxypyrrolidine (0.01 g, 0.047 mmol) and triethylamine (13.1 μL, 0.0938 mmol) in tetrahydrofuran (3 ml), was added iodoethane (5.6 μL, 0.070 mmol). The resulting mixture was stirred at ambient temperature for 24 h and then diluted with methanol and analyzed by GCMS and LCMS. Analysis show 64% conversion. MS m/z (relative intensity, 70 eV) 241 (M+, 10), 226 (86), 211 (33), 141 (49), 71 (bp).

Sources & evidence

ORD record
ord-536c84e5ce7c4ec596d4f684cfe77cdb
Source dataset
uspto-grants-2014_03
Patent number
US08673962B2

Reaction notes

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