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

HRID 29759

反応式

HRID 29759 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-4957361cdce74dd4a55bb646c85e54e8
出典データセット
uspto-grants-2008_09
特許番号
US07423012B2

関連ノート

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