반응 #54346

ord-8b69a75568a74b1c9e91c4639bbb9fe6

반응 방정식

[Br][Mg][CH2]CCc1ccccc1
3-phenylpropylmagnesium bromide
CCCCCCC(C)(C)c1ccc(C2CN(Cc3ccccc3)CCC2=O)c(OCc2ccccc2)c1
1-benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidone
C1CCOC1
tetrahydrofuran
[Cl-].[NH4+]
ammonium chloride
C1CCOC1
tetrahydrofuran
CCCCCCC(C)(C)c1ccc(C2CN(Cc3ccccc3)CCC2(O)CCCc2ccccc2)c(OCc2ccccc2)c1
title compound
CCCCCCC(C)(C)c1ccc(C2CN(Cc3ccccc3)CCC2(O)CCCc2ccccc2)c(OCc2ccccc2)c1
1-Benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-(3-phenylpropyl)-4-piperidinol

용매

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타To a 0° C.
  2. 2
    workup.ADDITIONis then added to 250 ml
  3. 3
    건조The ether phase is dried over magnesium sulfate
  4. 4
    기타evaporated
  5. 5
    기타The residue is purified via column chromatography on 200 g
  6. 6
    세척of silica gel eluted with 50% ether-cyclohexane

실험 절차

To a 0° C. solution of 7.0 mmols. of 3-phenylpropylmagnesium bromide in 7 ml. of tetrahydrofuran is slowly added a solution of 2.48 g. (5.0 mmols.) of 1-benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidone in 10 ml. of tetrahydrofuran. The resultant mixture is stirred for one hour and is then added to 250 ml. of saturated ammonium chloride-250 ml. ether. The ether phase is dried over magnesium sulfate and evaporated. The residue is purified via column chromatography on 200 g. of silica gel eluted with 50% ether-cyclohexane to yield the title compound.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US04147872uspto-grants-1979_04