Sodium triacetoxyborohydride → (4R,7R,8aS)-4-benzhydryl-7-[(tert-butyldimethylsilyl)oxy]-2-[2-methoxy-5-[5-(trifluoromethyl)-1H-tetrazol-1-yl]benzyl]-octahydropyrrolo[1,2-a]pyrazine

HRID 1006353ノート

反応式

HRID 1006353 の反応式
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH:15]([CH:28]1[N:33]2[CH2:34][C@H:35]([O:37][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])[CH2:36][C@H:32]2[CH2:31][NH:30][CH2:29]1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH3:45][O:46][C:47]1[CH:54]=[CH:53][C:52]([N:55]2[C:59]([C:60]([F:63])([F:62])[F:61])=[N:58][N:57]=[N:56]2)=[CH:51][C:48]=1[CH:49]=O>ClCCl>[CH:15]([C@H:28]1[N:33]2[CH2:34][C@H:35]([O:37][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])[CH2:36][C@H:32]2[CH2:31][N:30]([CH2:49][C:48]2[CH:51]=[C:52]([N:55]3[C:59]([C:60]([F:63])([F:62])[F:61])=[N:58][N:57]=[N:56]3)[CH:53]=[CH:54][C:47]=2[O:46][CH3:45])[CH2:29]1)([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

5

反応物 3

HCID 5049666Sodium triacetoxyborohydrideHCID 113916182-Methoxy-5-[5-(trifluoromethyl)tetrazol-1-yl]benzaldehydeHCID 69818675(7R,8aS)-4-benzhydryl-7-[(tert-butyldimethylsilyl)oxy)octahydropyrrolo[1,2-a]pyrazine

生成物 1

HCID 18346135(4R,7R,8aS)-4-benzhydryl-7-[(tert-butyldimethylsilyl)oxy]-2-[2-methoxy-5-[5-(trifluoromethyl)-1H-tetrazol-1-yl]benzyl]-octahydropyrrolo[1,2-a]pyrazine収率 34.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Sodium triacetoxyborohydride (163 mg) was added to a mixture of bis(acetic acid) salt of (7R,8aS)-4-benzhydryl-7-[(tert-butyldimethylsilyl)oxy]octahydropyrrolo[1,2-a]pyrazine (0.38 g) and 2-methoxy-5-[5-(trifluoromethyl)-1H-tetrazol-1-yl]benzaldehyde (210 mg) in dichloromethane, and the whole was stirred for 3 hours at room temperature. The mixture was washed with aqueous sodium hydrogen carbonate, dried over magnesium sulfate and concentrated under reduced pressure. The syrup was purified by column chromatography on silica gel using a mixed solvent of hexane and ethyl acetate (4:1). The later eluting fractions were collected and evaporated under reduced pressure to give colorless oil of (4R,7R,8aS)-4-benzhydryl-7-[(tert-butyldimethylsilyl)oxy]-2-[2-methoxy-5-[5-(trifluoromethyl)-1H-tetrazol-1-yl]benzyl]-octahydropyrrolo[1,2-a]pyrazine (0.18 g).

後処理

  1. washThe mixture was washed with aqueous sodium hydrogen carbonate
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe syrup was purified by column chromatography on silica gel using a mixed solvent of hexane and ethyl acetate (4:1)
  5. washThe later eluting fractions
  6. customwere collected
  7. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-10d42f07c10f4745ba5ca9bca4e98ce1
出典データセット
uspto-grants-2004_09
特許番号
US06787543B2

反応ノート

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