1,1-Dibromoethane → Benzyl 3-phenylpropanoate

HRID 1594655Notes

Reaction equation

HRID 1594655 reaction equation
BrC(Br)C.[CH2:5]([O:12][C:13](=[O:25])[C@H:14]([CH3:24])N(I)C(OC(C)(C)C)=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.I[C:27]1[CH:32]=[CH:31][C:30](C2(C([O-])=O)CC2)=[CH:29][CH:28]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C1COCC1.CC(N(C)C)=O.C(OCC)(=O)C.[Zn].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:5]([O:12][C:13](=[O:25])[CH2:14][CH2:24][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

10

Reactant 4

HCID 112011,1-DibromoethaneHCID 80271Tri-o-tolylphosphineHCID 21968199N-Boc-iodo-L-alanine benzyl esterHCID 863308141-(4-Iodophenyl)cyclopropane-1-carboxylate

Product 1

HCID 562789Benzyl 3-phenylpropanoateYield 67.1%

Reagents, catalysts & solvents 5

HCID 23994ZincCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent2×

Conditions

Temperature
55 °C

Procedure

A suspension of zinc (0.874 g) in THF with dibromoethane (0.02 mL) was sonicated at 40° C. for 40 minutes under argon. N-Boc-iodo-L-alanine benzyl ester (4.20 g, 10.4 mmol) and dimethylacetamide (5 mL) were added, and the mixture was heated at 55° C. for 1 hour. tbutyl 1-(4-iodophenyl)cyclopropane-1-carboxylate (3.26 g, 9.48 mmol) in dimethylacetamide (10 mL) was added followed by tris(dibenzylideneacetone)dipalladium(0) (0.33 g) and tri-o-tolylphosphine (0.398 g). Heating was continued under argon for 16 hours. The mixture was diluted with ethyl acetate, washed with water, dried, filtered and evaporated. Chromatography of the residue over silica gel (methylene chloride/hexane 1/3 to methylene chloride/ethyl acetate 95/5) gave 2-(S)-tbutoxycarbonylamino-3-[4′-1″-tbutoxycarbonyl)cyclopropyl]benzenepropanoic acid benzyl ester (3.15 g, 6.36 mmol, 67%).

Workup

  1. customwas sonicated at 40° C. for 40 minutes under argon
  2. temperatureHeating
  3. washwashed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-ac383dfc05024e9b8a6d92147fbc163f
Source dataset
uspto-grants-2001_09
Patent number
US06284768B1

Reaction notes

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