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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
ノート
印刷プレビュー

反応式

HRID 1669450 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒
HCID 8857
Ethyl Acetate
溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-6fae9a1e43ca4bbe8b0b1d98f85da984
出典データセット
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07989438B2

反応ノート

読み込み中…

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