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

HRID 575950Notes

Reaction equation

HRID 575950 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-6c78d5082c794f14914a57670b44488b
Source dataset
uspto-grants-2015_05
Patent number
US09035073B2

Reaction notes

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