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Potassium Hydroxide → (R)-1-[1-benzyl-3-(1-methyl-2-pyrrolidinylmethyl)-1H-indol-5-yl]-N-diphenylmethyl-N-methylmethanesulfonamide

HRID 651701
ノート
印刷プレビュー

反応式

HRID 651701 の反応式
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH:17](C#N)[S:18]([N:21]([CH:23]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH3:22])(=[O:20])=[O:19])=[CH:14][CH:15]=2)[C:10]([CH2:38][C@H:39]2[CH2:43][CH2:42][CH2:41][N:40]2[CH3:44])=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>C(O)C>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][S:18]([N:21]([CH:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH3:22])(=[O:19])=[O:20])=[CH:14][CH:15]=2)[C:10]([CH2:38][C@H:39]2[CH2:43][CH2:42][CH2:41][N:40]2[CH3:44])=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 14797Potassium HydroxideHCID 540937701-[(R)-1-benzyl-3-(1-methyl-2-pyrrolidinylmethyl)-1H-indol-5-yl]-1-cyano-N-diphenylmethyl-N-methylmethanesulfonamide

生成物 1

HCID 57119402(R)-1-[1-benzyl-3-(1-methyl-2-pyrrolidinylmethyl)-1H-indol-5-yl]-N-diphenylmethyl-N-methylmethanesulfonamide収率 61.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

To a stirred solution of 1-[(R)-1-benzyl-3-(1-methyl-2-pyrrolidinylmethyl)-1H-indol-5-yl]-1-cyano-N-diphenylmethyl-N-methylmethanesulfonamide (from step (d), 11.61 g, 19.3 mmol) in ethanol (35 ml) at ambient temperature was added 2N potassium hydroxide solution (35 ml, 70 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 (3×100 ml). The organic extracts were combined and evaporated in vacuo to yield the crude product as a dark brown oil. The oil was diluted with ethanol (35 ml) and stirred at ambient temperature for 12 hr, which resulted in precipitation. The mixture was then filtered and the solid dried in vacuo at 50° C. overnight to yield the title compound (6.82 g, 61%) as a beige solid. m.p. 117-120° C.

後処理

  1. temperatureto reflux
  2. temperaturemaintained at this temperature for 15 hr
  3. extractionextracted with ethyl acetate (3×100 ml)
  4. customevaporated in vacuo
  5. customto yield the crude product as a dark brown oil
  6. customwhich resulted in precipitation
  7. filtrationThe mixture was then filtered
  8. customthe solid dried in vacuo at 50° C. overnight

出典と根拠

ORDレコード
ord-3185ec7fc159400bbd32c45ca89e96cb
出典データセット
uspto-grants-2001_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06281357B1

反応ノート

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