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

HRID 38116

Reaction equation

HRID 38116 reaction equation
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

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 61668Boronic AcidHCID 86658779tert-butyl ((1R,2S)-2-(4-bromophenyl)cyclopropyl)carbamate2×

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-40bdd2650dc84da68d73597eb7e292c0
Source dataset
uspto-grants-2013_09
Patent number
US08524717B2

Linked notes

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