Iodoethane → 3-(2,3-Dichlorophenyl)-1-ethylpyrrolidin-3-ol

HRID 1931807Notes

Reaction equation

HRID 1931807 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1([OH:14])[CH2:13][CH2:12][NH:11][CH2:10]1.[C:15](#N)[CH3:16].C(=O)([O-])[O-].[K+].[K+].ICC>O>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1([OH:14])[CH2:13][CH2:12][N:11]([CH2:15][CH3:16])[CH2:10]1

Participants

6

Reactant 4

HCID 6340Iodoethane2×HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 635858853-(2,3-Dichlorophenyl)pyrrolidin-3-ol

Product 1

HCID 251436673-(2,3-Dichlorophenyl)-1-ethylpyrrolidin-3-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a sealed tube a mixture of 3-(2,3-dichlorophenyl)pyrrolidin-3-ol (0.35 g, 1.51 mmol), acetonitrile (20 mL), potassium carbonate (0.019 g, 3.77 mmol) and iodoethane (0.24 g, 1.51 mmol) was stirred at ambient temperature over night, additional iodoethane (0.02 mL) was added and the resulting mixture was stirred over night. Water (50 mL) was added, the aqueous phase was extracted with tert-butyl methyl ether (2×50 mL) and the combined organic phase was dried (MgSO4) and evaporated. Purification by flash column chromatography on silica gel (ethyl acetate/methanol, 1:0 to 1:1) gave the title compound (0.13 g). The amine was converted to the oxalic acid salt and recrystallized from methanol/ethanol/diethyl ether: M.p. 206-207° C.; MS m/z (relative intensity, 70 eV) 259 (M+, 5), 173 (7), 145 (6), 72 (23), 71 (bp).

Workup

  1. stirringthe resulting mixture was stirred over night
  2. extractionthe aqueous phase was extracted with tert-butyl methyl ether (2×50 mL)
  3. dry with materialthe combined organic phase was dried (MgSO4)
  4. customevaporated
  5. customPurification by flash column chromatography on silica gel (ethyl acetate/methanol, 1:0 to 1:1)

Sources & evidence

ORD record
ord-8458b114bd7044d68e5ffe3925349381
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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