Aluminium lithium hydride → (S)-(1-Formyl-3-methyl-butyl)-methyl-carbamic acid tert-butyl ester

HRID 990398ノート

反応式

HRID 990398 の反応式
[C:1]([O:5][C:6](=[O:20])[N:7]([C@H:9]([C:14](=[O:19])N(OC)C)[CH2:10][CH:11]([CH3:13])[CH3:12])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[C:1]([O:5][C:6](=[O:20])[N:7]([C@H:9]([CH:14]=[O:19])[CH2:10][CH:11]([CH3:12])[CH3:13])[CH3:8])([CH3:2])([CH3:4])[CH3:3]

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 53718737(S)-[1-(Methoxy-methyl-carbamoyl)-3-methyl-butyl]-methyl-carbamic acid tert-butyl ester

生成物 1

HCID 54220075(S)-(1-Formyl-3-methyl-butyl)-methyl-carbamic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
0 °C

実験手順

(S)-[1-(Methoxy-methyl-carbamoyl)-3-methyl-butyl]-methyl-carbamic acid tert-butyl ester (288 mg, 1.0 mmol) was dissolved in Et2O (10 mL), cooled to 0° C., treated with LAH (38 mg, 1.0 mmol), and stirred cold for 30 minutes. The reaction was quenched by dropwise addition of a solution of 150 mg Na2S2O3 in 5 mL H2O. The reaction was diluted with H2O (100 mL), washed with Et2O (3×100 mL), then the organic layers were combined, washed with saturated bicarbonate solution and brine, dried over Na2SO4, and concentrated to give the desired product which was carried on immediately without further purification.

後処理

  1. customThe reaction was quenched by dropwise addition of a solution of 150 mg Na2S2O3 in 5 mL H2O
  2. additionThe reaction was diluted with H2O (100 mL)
  3. washwashed with Et2O (3×100 mL)
  4. washwashed with saturated bicarbonate solution and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-5309e48acc1d49b89c642ed76a99e323
出典データセット
uspto-grants-2002_10
特許番号
US06458781B1

反応ノート

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