Lithium borohydride → HCID 69147839、化合物

HRID 747018ノート

反応式

HRID 747018 の反応式
C([O:4][CH:5]1[C:9]2([CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])[CH2:11][CH2:10]2)[C:8](=[O:25])[O:7][C:6]1([CH3:27])[CH3:26])(=O)C.[BH4-].[Li+]>O1CCCC1>[OH:4][CH:5]([C:9]1([CH2:8][OH:25])[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:11][CH2:10]1)[C:6]([OH:7])([CH3:27])[CH3:26]

参加物

4

反応物 2

HCID 4148881Lithium borohydrideHCID 69148927Benzyl 4-(acetyloxy)-3,3-dimethyl-1-oxo-2-oxa-8-azaspiro[4.5]decane-8-carboxylate

生成物 1

HCID 69147839HCID 69147839、化合物収率 27%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Benzyl 4-(acetyloxy)-3,3-dimethyl-1-oxo-2-oxa-8-azaspiro[4.5]decane-8-carboxylate (from step (i) above; 1.4 g) was dissolved in tetrahydrofuran and lithium borohydride (81 mg) was added. The mixture was heated under reflux for 2 h, cooled and quenched carefully with water and HCl (30 mL, 5N). The mixture was extracted with ethyl acetate and dried (MgSO4), and concentrated in vacuo. The crude product was purified by chromatography on silica using 2-5% methanol in dichloromethane as eluant to afford the product (340 mg).

後処理

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 h
  3. temperaturecooled
  4. customquenched carefully with water and HCl (30 mL, 5N)
  5. extractionThe mixture was extracted with ethyl acetate
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by chromatography on silica using 2-5% methanol in dichloromethane as eluant

出典と根拠

ORDレコード
ord-29e934fb82b74e38857915dd8f5efa37
出典データセット
uspto-grants-2008_07
特許番号
US07393858B2

反応ノート

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