Iodoethane → (2S, 4S)-2-Carbamoyl-1-ethyl-4-(4-methoxybenzylthio)pyrrolidine

HRID 1030157Notes

Reaction equation

HRID 1030157 reaction equation
[CH2:1](I)[CH3:2].C(=O)(O)[O-].[Na+].[C:9]([C@@H:12]1[CH2:16][C@H:15]([S:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH2:14][NH:13]1)(=[O:11])[NH2:10]>CN(C)C=O>[C:9]([C@@H:12]1[CH2:16][C@H:15]([S:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=2)[CH2:14][N:13]1[CH2:1][CH3:2])(=[O:11])[NH2:10]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 516892Sodium Bicarbonate2×HCID 14880267(2S, 4S)-2-Carbamoyl-4-(4-methoxybenzylthio)-pyrrolidine

Product 1

HCID 14796650(2S, 4S)-2-Carbamoyl-1-ethyl-4-(4-methoxybenzylthio)pyrrolidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.362 ml of ethyl iodide and 315 mg of sodium bicarbonate to a solution of 1000 mg of (2S, 4S)-2-carbamoyl-4-(4-methoxybenzylthio)pyrrolidine dissolved in 10 ml of dry dimethylformamide were added, whilst ice-cooling, and the mixture was stirred at room temperature for 5.5 hours. At the end of this time, the reaction mixture was poured into a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was removed by distillation under reduced pressure. The residue was subjected to column chromatography through silica gel (Katayama Chemicals Co., Silica Gel 60K070) and 560 mg of the title compound were obtained as crystals, melting at 124°-125° C., from the fractions eluted with ethyl acetate.

Workup

  1. additionwere added, whilst ice-
  2. temperaturecooling
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with an aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-1e0d593009a94ace91a19e00385aa4f4
Source dataset
uspto-grants-1992_04
Patent number
US05104867

Reaction notes

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