Water → Tert-butyl(trans)-2-(1,1'-biphenyl-4-yl)cyclopropylcarbamate

HRID 38116

반응식

HRID 38116 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:10][C@H:9]2[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:4][CH:3]=1.B(O)O.C([O-])([O-])=O.[K+].[K+].O>CC#N.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:2]1([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:10][C@H:9]2[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 61668Boronic AcidHCID 86658779tert-butyl ((1R,2S)-2-(4-bromophenyl)cyclopropyl)carbamate2회

생성물 1

HCID 86658778Tert-butyl(trans)-2-(1,1'-biphenyl-4-yl)cyclopropylcarbamate

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 18373917Acetonitrile--water (1/1)용매

실험 절차

A solution of tert-butyl(trans)-2-(4-bromophenyl)cyclopropylcarbamate (Intermediate F; 1 equiv), 1.2 equiv of the boronic acid, 3.0 equiv of K2CO3 in CH3CN+H2O (4:1) was degassed for 30 mins with Argon gas, added 0.01 equiv of Pd (PPh3)4, heated the reaction mixture at reflux temp for 4 h. The progress of the reaction was monitored by TLC, after completion, poured the reaction mixture into water, extracted with EtOAc. The combined extracts were washed with water, brine, dried over anhydrous Na2SO4, filtered and evaporated. The crude residue was purified by column chromatography to get tert-butyl(trans)-2-(1,1′-biphenyl-4-yl)cyclopropylcarbamate derivative

후처리

  1. temperatureheated the reaction mixture
  2. temperatureat reflux temp for 4 h
  3. extractionextracted with EtOAc
  4. washThe combined extracts were washed with water, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-40bdd2650dc84da68d73597eb7e292c0
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524717B2

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