1,1-Dichloroethane → 4-(Methoxycarbonyl)phenyl(3s,4s)-3-({[1-(1-benzothien-3-yl)ethyl]amino}methyl)-4-phenylpyrrolidine-1-carboxylate

HRID 732716ノート

反応式

HRID 732716 の反応式
ClC(Cl)C.[NH2:5][CH2:6][C@@H:7]1[C@@H:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:10][N:9]([C:18]([O:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([O:29][CH3:30])=[O:28])=[CH:23][CH:22]=2)=[O:19])[CH2:8]1.[C:31]([C:34]1[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=2[S:36][CH:35]=1)(=O)[CH3:32].[BH4-].[Na+]>CO.C(O[Ti](OC(C)C)(OC(C)C)OC(C)C)(C)C>[S:36]1[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[C:34]([CH:31]([NH:5][CH2:6][C@@H:7]2[C@@H:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:10][N:9]([C:18]([O:20][C:21]3[CH:22]=[CH:23][C:24]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:26]=3)=[O:19])[CH2:8]2)[CH3:32])=[CH:35]1

参加物

7

反応物 4

HCID 63651,1-DichloroethaneHCID 143163-AcetylbenzothiopheneHCID 4311764Sodium borohydrideHCID 68911676HCID 68911676、化合物

生成物 1

HCID 689115814-(Methoxycarbonyl)phenyl(3s,4s)-3-({[1-(1-benzothien-3-yl)ethyl]amino}methyl)-4-phenylpyrrolidine-1-carboxylate収率 55%

試薬・触媒・溶媒 2

HCID 178460666HCID 178460666、化合物触媒HCID 887Methanol溶媒

実験手順

A 1.0 ml dichloroethane solution of 119 mg of 4-(methoxycarbonyl)phenyl(3S,4S)-3-(aminomethyl)-4-phenylpyrrolidine-1-carboxylate and 62 mg of 3-acetylbenzothiophene was mixed with 0.12 ml of tetraisopropoxy titanium and stirred for 2 hours. The reaction solution was diluted with 1.0 ml of methanol, mixed with 38 mg of sodium borohydride, further stirred for 1 hour and then concentrated under a reduced pressure, and the thus obtained was purified by a silica gel chromatography (chloroform-methanol) to obtain 95 mg of 4-(methoxycarbonyl)phenyl(3S,4S)-3-({[1-(1-benzothien-3-yl)ethyl]amino}methyl)-4-phenylpyrrolidine-1-carboxylate as a yellow amorphous substance. EP: 515.

後処理

  1. stirringfurther stirred for 1 hour
  2. concentrationconcentrated under a reduced pressure
  3. customthe thus obtained
  4. customwas purified by a silica gel chromatography (chloroform-methanol)

出典と根拠

ORDレコード
ord-4b019befc9854dcc9b2ccdf87093c635
出典データセット
uspto-grants-2009_09
特許番号
US07585886B2

反応ノート

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