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

HRID 1188180Notes

Reaction equation

HRID 1188180 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 83% conversion. MS m/z (relative intensity, 70 eV) 257 (M+, 8), 242 (78), 227 (31), 157 (36), 71 (bp).

Workup

  1. customPreparation

Sources & evidence

ORD record
ord-42be5b2fc7ce4569b54ea251b32ca35b
Source dataset
uspto-grants-2014_03
Patent number
US08673962B2

Reaction notes

Loading…