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

HRID 334348

반응식

HRID 334348 반응식
[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]

참가 물질

7

반응물 4

HCID 784Hydrogen PeroxideHCID 1061PhosphateHCID 4304157Potassium;tri(butan-2-yl)boranuideHCID 67022408(3RS,4SR)-3-(3,4-dimethoxyphenyl)-4-nitrocyclohexanone2회

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c08233194c3142b88d6298b05a8b49fd
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883818B2

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