Iodoethane → HCID 46219099, compound

HRID 1188153Notes

Reaction equation

HRID 1188153 reaction equation
[Cl:1][C:2]1[C:3]([F:15])=[C:4]([C:8]2([O:13][CH3:14])[CH2:12][CH2:11][NH:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.I[CH2:17][CH3:18].C(N(CC)CC)C>O1CCCC1>[Cl:1][C:2]1[C:3]([F:15])=[C:4]([C:8]2([O:13][CH3:14])[CH2:12][CH2:11][N:10]([CH2:17][CH3:18])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 8471TriethylamineHCID 46196348HCID 46196348, compound

Product 1

HCID 46219099HCID 46219099, compoundYield 35.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Preparation according to Example 2. (−)-3-(3-chloro-2-fluorophenyl)-3-methoxypyrrolidine (0.234 g, 1.02 mmol), tetrahydrofuran (20 ml), iodoethane (0.122 ml, 1.15 mmol) and triethylamine (0.285 ml, 2.04 mmol), the solution was stirred for 26 h. Purification by HPLC on waters OBD C18, 5 μm (MeOH/33 mM NH3, 20:80 to 65:35) gave the title compound 0.094 g (35.9%). [a]D=−16.1° (methanol). The amine was converted to the fumaric acid salt and recrystallized from 2-propanol/diisopropyl ether: M.p. 131-133° C. MS m/z (rel. intensity, 70 eV) 257 (M+, 4), 242 (38), 227 (20), 157 (31), 71 (bp).

Workup

  1. customPreparation
  2. customPurification by HPLC on waters OBD C18, 5 μm (MeOH/33 mM NH3, 20:80 to 65:35)

Sources & evidence

ORD record
ord-a58ec77e42b64271ab8f3d579f8ce95b
Source dataset
uspto-grants-2014_03
Patent number
US08673962B2

Reaction notes

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