Bromobenzene → (+/-)-trans-1,2,3,4,4a,5,6,7,8,8a-Decahydro-2-ethyI-4a-(3-methoxyphenyl)-6-phenyl-6-isoquinolinol

HRID 1739783

반응식

HRID 1739783 반응식
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:13]([N:15]1[CH2:24][CH2:23][C@@:22]2([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[CH:26]=3)[C@@H:17]([CH2:18][CH2:19][C:20](=[O:33])[CH2:21]2)[CH2:16]1)[CH3:14]>CCCCCC.C1COCC1>[NH4+:15].[OH-:31].[CH2:13]([N:15]1[CH2:24][CH2:23][C@@:22]2([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[CH:26]=3)[C@@H:17]([CH2:18][CH2:19][C:20]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)([OH:33])[CH2:21]2)[CH2:16]1)[CH3:14]

참가 물질

7

반응물 3

HCID 7961BromobenzeneHCID 10517409(+/-)-trans-1,2,3,4,4a,5,6,7,8,8a-Decahydro-2-ethyl-4a-(3-methoxyphenyl)-6-isoquinolinoneHCID 178418339Butyllithium

생성물 2

HCID 14923Ammonium HydroxideHCID 86754625(+/-)-trans-1,2,3,4,4a,5,6,7,8,8a-Decahydro-2-ethyI-4a-(3-methoxyphenyl)-6-phenyl-6-isoquinolinol수율 52.1%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

반응 조건

온도
-20 °C

실험 절차

30 ml (41.7 mmol) of a 1.4 M solution of n-butyllithium in hexane were added dropwise, under a nitrogen atmosphere and at -55° C., to a solution of 6.5 g (41.7 mmol) of bromobenzene in 30 ml of dry THF. After 1 h the solution was allowed to warm up to -20° C. and a solution of 2.4 g (8.3 mmol) of (±)-trans-1,2,3,4,4a,5,6,7,8,8a-decahydro-2-ethyl-4a-(3-methoxyphenyl)-6-isoquinolinone in 20 ml of dry THF was added. The reaction mixture was allowed to warm up to room temperature overnight, then it was quenched with 30 ml of a 5% HCl solution and the phases were separated. The aqueous phase was extracted with AcOEt, then brought to pH 14 with a 2N NaOH solution and extracted with AcOEt. The organic phase was dried over Na2SO4 and the solvent was removed in vacuo. The crude reaction mixture was purified by flash chromatography, eluting with a mixture CH2Cl2 /MeOH/conc. NH4OH 90:7:0.7 respectively, yielding 0.79 g of the title compound.

후처리

  1. temperatureto warm up to room temperature overnight
  2. customit was quenched with 30 ml of a 5% HCl solution
  3. customthe phases were separated
  4. extractionThe aqueous phase was extracted with AcOEt
  5. extractionextracted with AcOEt
  6. dry with materialThe organic phase was dried over Na2SO4
  7. customthe solvent was removed in vacuo
  8. customThe crude reaction mixture
  9. customwas purified by flash chromatography
  10. washeluting with a mixture CH2Cl2 /MeOH/conc

출처 및 근거

ORD 기록
ord-2f8deed0a8bc40f196403bb5701a411d
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05968949

연결된 노트

불러오는 중…