(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 473058노트

반응식

HRID 473058 반응식
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]

참가 물질

6

반응물 1

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

생성물 1

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

시약·촉매·용매 4

HCID 180Acetone용매HCID 712Formaldehyde용매HCID 6395Methanesulfonic Acid용매HCID 23938Palladium용매

실험 절차

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

후처리

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

출처 및 근거

ORD 기록
ord-32d904fee3e54f058e09eed99808ceb3
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633239B2

반응 노트

불러오는 중…