Aluminium lithium hydride → racemic (2'R,3R,4'S)-6-chloro-4'-[5-chloro-2-(1-hydroxymethyl-cyclobutoxy)-phenyl]-2'-(5-fluoro-2-methyl phenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 1728233

반응식

HRID 1728233 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Cl:7][C:8]1[CH:13]=[C:12]2[NH:14][C:15](=[O:47])[C:16]3([CH:21]([C:22]4[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:23]=4[O:29][C:30]4([C:34](OC)=[O:35])[CH2:33][CH2:32][CH2:31]4)[CH2:20][C:19](=[O:38])[NH:18][CH:17]3[C:39]3[CH:44]=[C:43]([F:45])[CH:42]=[CH:41][C:40]=3[CH3:46])[C:11]2=[CH:10][CH:9]=1>C1COCC1>[Cl:7][C:8]1[CH:13]=[C:12]2[NH:14][C:15](=[O:47])[C:16]3([CH:21]([C:22]4[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:23]=4[O:29][C:30]4([CH2:34][OH:35])[CH2:33][CH2:32][CH2:31]4)[CH2:20][C:19](=[O:38])[NH:18][CH:17]3[C:39]3[CH:44]=[C:43]([F:45])[CH:42]=[CH:41][C:40]=3[CH3:46])[C:11]2=[CH:10][CH:9]=1

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 765679126-chloro-4'-[5-chloro-2-(1-methoxycarbonyl-cyclobutoxy)-phenyl]-2'-(5-fluoro-2-methyl-phenyl)-spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

생성물 1

HCID 76568037racemic (2'R,3R,4'S)-6-chloro-4'-[5-chloro-2-(1-hydroxymethyl-cyclobutoxy)-phenyl]-2'-(5-fluoro-2-methyl phenyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione수율 24.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of LiAlH4 (15 mg, 0.4 mmol) in THF (2 mL) was added racemic (2′S,3S,4′R)-6-chloro-4′-[5-chloro-2-(1-methoxycarbonyl-cyclobutoxy)-phenyl]-2′-(5-fluoro-2-methyl-phenyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (RO5247453-000) (60 mg, 0.1 mmol). The mixture was stirred in a ice bath for 1.5 h, quenched with MeOH, purified by Prep-HPLC to give title compound (14 mg, 24%). m/z (M+H)+: 569

후처리

  1. customquenched with MeOH
  2. custompurified by Prep-HPLC

출처 및 근거

ORD 기록
ord-95137d91a37c44aa971d6087b8ef384c
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07495007B2

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