Potassium Hydroxide → (r)-n-Benzyl-1-[1-benzyl-3-(1-methyl-2-pyrrolidinylmethyl)-1h-indol-5-yl]-n-methylmethanesulfonamide

HRID 651696노트

반응식

HRID 651696 반응식
[CH2:1]([N:8]([CH3:38])[S:9]([CH:12]([C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[N:20]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:19]=[C:18]2[CH2:31][C@H:32]1[CH2:36][CH2:35][CH2:34][N:33]1[CH3:37])C#N)(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>C(O)C>[CH2:1]([N:8]([CH3:38])[S:9]([CH2:12][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[N:20]([CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH:19]=[C:18]2[CH2:31][C@H:32]1[CH2:36][CH2:35][CH2:34][N:33]1[CH3:37])(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 14797Potassium HydroxideHCID 59966110N-Benzyl-1-[(R)-1-benzyl-3-(1-methyl-2-pyrrolidinylmethyl)-1H-indol-5-yl]-1-cyano-N-methylmethanesulfonamide

생성물 1

HCID 53689728(r)-n-Benzyl-1-[1-benzyl-3-(1-methyl-2-pyrrolidinylmethyl)-1h-indol-5-yl]-n-methylmethanesulfonamide수율 89.2%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a stirred solution of N-benzyl-1-[(R)-1-benzyl-3-(1-methyl-2-pyrrolidinylethyl)-1H-indol-5-yl]-1-cyano-N-methylmethanesulfonamide (from step (e), 29 g, 55.1 mmol) in ethanol (200 ml) at ambient temperature was added 2N potassium hydroxide solution (200 ml, 400 mmol). The dark brown solution was then brought to reflux and maintained at this temperature for 15 hr. The oily reaction mixture was then cooled to ambient temperature and extracted with ethyl acetate (3×300 ml). The organic extracts where combined and evaporated in vacuo to give a dark brown oil. This was purified by flash column chromatography (ethyl acetate:hexane:diethylamine 1:1:0.1 as eluant) to yield the subtitle compound (24.67 g, 89%) as a brown oil.

후처리

  1. temperatureto reflux
  2. temperaturemaintained at this temperature for 15 hr
  3. extractionextracted with ethyl acetate (3×300 ml)
  4. customevaporated in vacuo
  5. customto give a dark brown oil
  6. customThis was purified by flash column chromatography (ethyl acetate:hexane:diethylamine 1:1:0.1 as eluant)

출처 및 근거

ORD 기록
ord-2254eabbd0054d118596728c74e69362
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06281357B1

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