Methyl iodide → (2S, 4S)-2-(N,N-Dimethylcarbamoyl)-4-(4-methoxybenzylthio)-1-methylpyrrolidine

HRID 1030142노트

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HRID 1030142 반응식
[C:1](=O)(O)[O-].[Na+].CI.[CH3:8][N:9]([CH3:27])[C:10]([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]>CN(C)C=O>[CH3:8][N:9]([CH3:27])[C:10]([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[CH3:1])=[O:11]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 516892Sodium Bicarbonate2회HCID 57025397(2S, 4S)-2-(N,N-Dimethylcarbamoyl)-4-(4-methoxybenzylthio)pyrrolidine

생성물 1

HCID 57114883(2S, 4S)-2-(N,N-Dimethylcarbamoyl)-4-(4-methoxybenzylthio)-1-methylpyrrolidine수율 26.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

84 mg of sodium bicarbonate and 41 μl of methyl iodide were added, whilst ice-cooling, to a solution of 163 mg of (2S, 4S)-2-(N,N-dimethylcarbamoyl)-4-(4-methoxybenzylthio)pyrrolidine [prepared as described in step (4) above] dissolved in 1.5 ml of dry dimethylformamide, and the mixture was stirred at room temperature for 4 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. The solvent was then removed by distillation under reduced pressure, and the residue was purified by chromatography using a Lobar column (Merck, LiChroprep Si60, size A). 45 mg of the title compound were obtained, as an oil, from the fractions eluted with a 3:1 by volume mixture of ethyl acetate and methanol.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with an aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was then removed by distillation under reduced pressure
  5. customthe residue was purified by chromatography

출처 및 근거

ORD 기록
ord-86f0ebe7d3df4da7b174397eb0c20895
출처 데이터셋
uspto-grants-1992_04
특허 번호
US05104867

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