Phosphate → (1RS,3RS,4RS)-3-(3,4-dimethoxyphenyl)-4-nitrocyclohexanol

HRID 73494

반응식

HRID 73494 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+].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

6

반응물 3

HCID 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% hydrogeneperoxide 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-f1f84741467349f1be779e3bcf9cacad
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829189B2

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