Dichloromethane → Methyl 3-(1-((tert-butoxycarbonyl)amino)ethyl)benzoate

HRID 1255833Notes

Reaction equation

HRID 1255833 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])[CH:5]=[CH:6][CH:7]=1.ClCCl.C(N(CC)CC)C>CO>[C:13]([O:12][C:11]([NH:10][CH:8]([C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[C:11]([O:12][CH3:13])=[O:17])[CH3:9])=[O:17])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 20744379tert-Butyl (1-(3-bromophenyl)ethyl)carbamate

Product 1

HCID 68656133Methyl 3-(1-((tert-butoxycarbonyl)amino)ethyl)benzoateYield 150.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 1-(3-bromophenyl)ethylcarbamate (300 mg, 1 mmol) in methanol (10 mL) was added [1,1′-bis(diphenyl-phosphino)ferrocene]palladium [II]chloride, 1:1 complex with dichloromethane (146 mg, 0.2 mmol) then triethylamine (0.28 mL, 2 mmol). The mixture was evacuated and backfilled with carbon monoxide four times and was then heated to reflux and stirred under an atmosphere of carbon monoxide for 17 hours. After this time the mixture was filtered through Celite to give a brown solid which was purified by flash chromatography (silica, ethyl acetate/hexanes) to give methyl 3-{1-[(tert-butoxycarbonyl)amino]ethyl}benzoate (210 mg, 75%) as a white solid.

Workup

  1. customThe mixture was evacuated
  2. temperaturewas then heated
  3. temperatureto reflux
  4. filtrationAfter this time the mixture was filtered through Celite
  5. customto give a brown solid which
  6. customwas purified by flash chromatography (silica, ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-df91893289244feba113bc6a74a0a7c8
Source dataset
uspto-grants-2013_06
Patent number
US08461161B2

Reaction notes

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