Aluminium lithium hydride → rac-tert-butyl N-[(1r,4r)-4-formylcyclohexyl]carbamate

HRID 899061

反応式

HRID 899061 の反応式
[C:1]([O:5][C:6](=[O:20])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:19])N(OC)C)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[C:1]([O:5][C:6](=[O:20])[NH:7][CH:8]1[CH2:9][CH2:10][CH:11]([CH:14]=[O:19])[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 24720928Tert-butyl trans-4-(N-methoxy-N-methylcarbamoyl)cyclohexylcarbamate

生成物 1

HCID 11020615rac-tert-butyl N-[(1r,4r)-4-formylcyclohexyl]carbamate収率 105.8%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

[4-(Methoxy-methyl-carbamoyl)-cyclohexyl]-carbamic acid tert-butyl ester (7.50 g, 26.2 mmol) in dry ether (150 ml) was reduced with an excess LiAlH4. The reaction mixture was quenched by careful addition of water and extracted with CHCl3. The mixture was dried and concentrated under reduced pressure to give (4-formyl-cyclohexyl)-carbamic acid tert-butyl ester (6.30 g, 93%).

後処理

  1. customThe reaction mixture was quenched by careful addition of water
  2. extractionextracted with CHCl3
  3. customThe mixture was dried
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-4d93907370f845c88920ef53642a78fa
出典データセット
uspto-grants-2008_04
特許番号
US07354895B1

関連ノート

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