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

HRID 651696ノート

反応式

HRID 651696 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-2254eabbd0054d118596728c74e69362
出典データセット
uspto-grants-2001_08
特許番号
US06281357B1

反応ノート

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