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Acetic Acid → methyl (7S)-14-cyclohexyl-7-(pyrrolidin-2-ylmethoxy)-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

HRID 1669450
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HRID 1669450 반응식
C([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[CH2:13][O:14][C@H:15]1[CH2:22][N:21]2[C:23]3[CH:24]=[C:25]([C:36]([O:38][CH3:39])=[O:37])[CH:26]=[CH:27][C:28]=3[C:29]([CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)=[C:20]2[C:19]2[CH:40]=[CH:41][CH:42]=[CH:43][C:18]=2[O:17][CH2:16]1)C1C=CC=CC=1.CC(O)=O>CCOC(C)=O.[OH-].[OH-].[Pd+2]>[CH:30]1([C:29]2[C:28]3[CH:27]=[CH:26][C:25]([C:36]([O:38][CH3:39])=[O:37])=[CH:24][C:23]=3[N:21]3[C:20]=2[C:19]2[CH:40]=[CH:41][CH:42]=[CH:43][C:18]=2[O:17][CH2:16][C@@H:15]([O:14][CH2:13][CH:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)[CH2:22]3)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]1
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참가 물질

5

반응물 2

HCID 176Acetic AcidHCID 67344945methyl (7S)-7-[(1-benzylpyrrolidin-2-yl)methoxy]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate

생성물 1

HCID 67345272methyl (7S)-14-cyclohexyl-7-(pyrrolidin-2-ylmethoxy)-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate수율 50%

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매
HCID 8857
Ethyl Acetate
용매

실험 절차

To a solution of methyl (7S)-7-[(1-benzylpyrrolidin-2-yl)methoxy]-14-cyclohexyl-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxylate (0.07 M) in EtOAc, was added an excess of AcOH (>50 eq) and Pd(OH)2/C. The atmosphere in the reaction flask was charged with H2 and the reaction stirred vigorously under a H2 atmosphere (balloon) at RT for 2 d. The mixture was filtered and the filtrate concentrated in vacuo. The crude was purified by FC (gradient from EtOAc/PE 6:4+1% NEt3 to EtOAc/PE 8:2+1% NEt3+5% MeOH) to afford the product (50%). (ES+) m/z 489 (M+H)+.

후처리

  1. additionThe atmosphere in the reaction flask was charged with H2
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe crude was purified by FC (gradient from EtOAc/PE 6:4+1% NEt3 to EtOAc/PE 8:2+1% NEt3+5% MeOH)

출처 및 근거

ORD 기록
ord-6fae9a1e43ca4bbe8b0b1d98f85da984
출처 데이터셋
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07989438B2

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