Hydrochloric Acid → (1RS,2SR,6RS,7RS)-8-(4-fluorophenyl)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.02,6]dec-8-en-3,5-dione

HRID 407857노트

반응식

HRID 407857 반응식
Br[C:2]1[CH:3]2[O:11][CH:9]([CH:10]=1)[CH:8]1[CH:4]2[C:5](=[O:22])[CH:6]([C:13]2[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=2[CH3:21])[C:7]1=[O:12].[F:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.O.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=C(S([O-])(=O)=O)C=2OC)CCCCC1.[Na+].P([O-])([O-])([O-])=O.[K+].[K+].[K+].Cl>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:23][C:24]1[CH:29]=[CH:28][C:27]([C:2]2[CH:3]3[O:11][CH:9]([CH:10]=2)[CH:8]2[CH:4]3[C:5](=[O:22])[CH:6]([C:13]3[C:14]([CH3:21])=[CH:15][C:16]([CH3:20])=[CH:17][C:18]=3[CH3:19])[C:7]2=[O:12])=[CH:26][CH:25]=1

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 62657Potassium Phosphate, TribasicHCID 2856454-Fluorophenylboronic acidHCID 23693092Sodium 2'-(dicyclohexylphosphanyl)-2,6-dimethoxy(1,1'-biphenyl)-3-sulfonate--water (1/1/1)HCID 67284125(1RS, 2RS,6SR,7SR)-8-bromo-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.02,6]dec-8-en-3,5-dione

생성물 1

HCID 67283881(1RS,2SR,6RS,7RS)-8-(4-fluorophenyl)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.02,6]dec-8-en-3,5-dione

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 962Water용매

반응 조건

온도
150 °C

실험 절차

A mixture of (1RS,2RS,6SR,7SR)-8-bromo-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.02,6]dec-8-en-3,5-dione (300 mg, 0.82 mmol), 4-fluorophenylboronic acid (171 mg, 1.22 mmol), sodium 2′-dicyclohexylphosphino-2,6-dimethoxy-1,1-biphenyl-3-sulfonate hydrate (17 mg, 0.03 mmol), potassium phosphate (522 mg, 2.5 mmol) and palladium acetate (4 mg, 0.02 mmol) in water (8 ml) are heated for 150° C. for 25 minutes under microwave irradiation. The mixture is cooled to room temperature and dilute aqueous hydrochloric acid is added. The mixture is filtered and the filtrate is extracted with ethyl acetate. The organic extracts are combined, dried over anhydrous magnesium sulfate, filtered and the filtrate is concentrated under reduced pressure. Purification by column chromatography on silica gel gives (1RS,2SR,6RS,7RS)-8-(4-fluorophenyl)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.02,6]dec-8-en-3,5-dione.

후처리

  1. temperatureThe mixture is cooled to room temperature
  2. filtrationThe mixture is filtered
  3. extractionthe filtrate is extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated under reduced pressure
  7. customPurification by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-3cbf642752874ed7bf5be552f8d94916
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754242B2

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