(R)-benzyl-2-(5-(2-(phenylsulfonyl)ethyl)-1H-indole-3-carbonyl)-pyrrolidine-1-carboxylate → (R)-(1-methylpyrrolidin-2-yl)(5-(2-(phenylsulfonyl)ethyl)-1H-indol-3-yl)methanone

HRID 473058ノート

反応式

HRID 473058 の反応式
C(O[C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@@H:12]1[C:16]([C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([CH2:27][CH2:28][S:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)(=[O:31])=[O:30])[CH:25]=2)[NH:20][CH:19]=1)=[O:17])=O)C1C=CC=CC=1>CC(C)=O.CS(O)(=O)=O.C=O.[Pd]>[CH3:9][N:11]1[CH2:15][CH2:14][CH2:13][C@@H:12]1[C:16]([C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([CH2:27][CH2:28][S:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)(=[O:30])=[O:31])[CH:25]=2)[NH:20][CH:19]=1)=[O:17]

参加物

6

反応物 1

HCID 46195789(R)-benzyl-2-(5-(2-(phenylsulfonyl)ethyl)-1H-indole-3-carbonyl)-pyrrolidine-1-carboxylate

生成物 1

HCID 9908745(R)-(1-methylpyrrolidin-2-yl)(5-(2-(phenylsulfonyl)ethyl)-1H-indol-3-yl)methanone収率 65%

試薬・触媒・溶媒 4

HCID 180Acetone溶媒HCID 712Formaldehyde溶媒HCID 6395Methanesulfonic Acid溶媒HCID 23938Palladium溶媒

実験手順

A suspension of (R)-benzyl-2-(5-(2-(phenylsulfonyl)ethyl)-1H-indole-3-carbonyl)-pyrrolidine-1-carboxylate (5.0 g) in 50 ml acetone, methanesulfonic acid, formaldehyde and 10% Pd/C was subject to hydrogenation at 45 psi. Upon completion of the reaction the catalyst was filtered off and the solvent removed under vacuum to provide the title compound in about 65-75% yield. Mass (M+Na) 419.5

後処理

  1. customUpon completion of the reaction the catalyst
  2. filtrationwas filtered off
  3. customthe solvent removed under vacuum

出典と根拠

ORDレコード
ord-32d904fee3e54f058e09eed99808ceb3
出典データセット
uspto-grants-2014_01
特許番号
US08633239B2

反応ノート

読み込み中…