Hydrogen Peroxide → (1RS,3RS,4RS)-3-(3,4-dimethoxyphenyl)-4-nitrocyclohexanol

HRID 334348

反応式

HRID 334348 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[CH:16]([N+:17]([O-:19])=[O:18])[CH2:15][CH2:14][C:13](=[O:20])[CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C([BH-](C(CC)C)C(CC)C)(CC)C.[K+].OO.P([O-])([O-])([O-])=O>O1CCCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]2[CH:16]([N+:17]([O-:19])=[O:18])[CH2:15][CH2:14][CH:13]([OH:20])[CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

参加物

7

反応物 4

HCID 784Hydrogen PeroxideHCID 1061PhosphateHCID 4304157Potassium;tri(butan-2-yl)boranuideHCID 67022408(3RS,4SR)-3-(3,4-dimethoxyphenyl)-4-nitrocyclohexanone2 回

生成物 1

HCID 17989075(1RS,3RS,4RS)-3-(3,4-dimethoxyphenyl)-4-nitrocyclohexanol

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
78 °C

実験手順

Under nitrogen atmosphere 16.76 g of (3RS,4SR)-3-(3,4-dimethoxyphenyl)-4-nitrocyclohexanone (compound F2) are dissolved in 300 ml of tetrahydrofurane, the solution is cooled to 78° C., and 75 ml of 1 M solution of potassium tri-sec-butylborohydride in tetrahydrofurane is added dropwise. After stirring for further 1 h, a mixture consisting of 30% hydrogen peroxide solution and phosphate buffer solution is added. Stirring is continued for further 10 min, the reaction mixture is diluted with 400 ml of ethyl acetate and the aqueous layer is extracted with ethyl acetate, the combined organic phases are concentrated to give a foam, which is purified by chromatography on silica gel using a mixture of petroleum ether/ethyl acetate in the ratio 1/1 to furnish 10.18 g (60% of theory) of the title compound.

後処理

  1. additionis added
  2. stirringStirring
  3. waitis continued for further 10 min
  4. extractionthe aqueous layer is extracted with ethyl acetate
  5. concentrationthe combined organic phases are concentrated
  6. customto give a foam, which
  7. customis purified by chromatography on silica gel using
  8. additiona mixture of petroleum ether/ethyl acetate in the ratio 1/1

出典と根拠

ORDレコード
ord-c08233194c3142b88d6298b05a8b49fd
出典データセット
uspto-grants-2014_11
特許番号
US08883818B2

関連ノート

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