Iodoethane → 3-(3-Chloro-5-fluorophenyl)-1-ethyl-3-methoxypyrrolidine

HRID 575966Notes

Reaction equation

HRID 575966 reaction equation
[Cl: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>[Cl: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

5

Reactant 3

HCID 6340IodoethaneHCID 8471TriethylamineHCID 462192233-(3-Chloro-5-fluorophenyl)-3-methoxypyrrolidine

Product 1

HCID 462193573-(3-Chloro-5-fluorophenyl)-1-ethyl-3-methoxypyrrolidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Preparation according to Example 22. (+)-3-(3-chloro-5-fluorophenyl)-3-methoxypyrrolidine (0.01 g, 0.043 mmol), triethylamine (12.1 μL, 0.086 mmol), tetrahydrofuran (2 ml) and iodoethane (5.2 μL, 0.065 mmol). The crude product analyzed by GCMS. Analysis showed 74% conversion. MS m/z (relative intensity, 70 eV) 257 (M+, 10), 242 (94), 227 (39), 157 (40), 71 (bp).

Workup

  1. customPreparation

Sources & evidence

ORD record
ord-c35b1244740c4c5cafc38d5991e6e73c
Source dataset
uspto-grants-2015_05
Patent number
US09035073B2

Reaction notes

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