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Diisobutylaluminumhydride → tert-butyl 6-(2-hydroxyethyl)-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate

HRID 1356247
ノート
印刷プレビュー

反応式

HRID 1356247 の反応式
C([O:3][C:4](=O)[CH2:5][N:6]1[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:8]2[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19][C:7]1=2)C.[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1.ClCCl>[OH:3][CH2:4][CH2:5][N:6]1[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:8]2[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19][C:7]1=2
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 21225700DiisobutylaluminumhydrideHCID 22396754tert-butyl 6-(2-ethoxy-2-oxoethyl)-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate

生成物 1

HCID 22396751tert-butyl 6-(2-hydroxyethyl)-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A chilled (0° C. ) mixture of tert-butyl 6-(2-ethoxy-2-oxoethyl)-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate in tetrahydrofuran (30 mL) was treated over 1 h with 1 M diisobutylaluminum hydride (19.0 mL, 19.0 mmol) in dichloromethane. After 1.5 h, ice was added and the mixture was allowed to warm to rt. The mixture was evaporated in vacuo and the residue was partitioned between ethyl acetate and water. The organic phase was filtered through celite, dried, and evaporated in vacuo to provide 2.479 g of the title compound, the structure of which is shown in FIG. 6 as (24) (where n=1).

後処理

  1. temperatureA chilled
  2. additionice was added
  3. customThe mixture was evaporated in vacuo
  4. customthe residue was partitioned between ethyl acetate and water
  5. filtrationThe organic phase was filtered through celite
  6. customdried
  7. customevaporated in vacuo

出典と根拠

ORDレコード
ord-8786396720d64acbaae624a20349ec14
出典データセット
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06586421B2

反応ノート

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