Allyl-pent-4-enyl-carbamic acid benzyl ester → 2,3,4,7-Tetrahydro-azepine-1-carboxylic acid benzyl ester

HRID 460402Notes

Reaction equation

HRID 460402 reaction equation
[CH2:1]([O:8][C:9](=[O:19])[N:10]([CH2:16][CH:17]=[CH2:18])[CH2:11][CH2:12][CH2:13]C=C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>ClCCl.C1CCC([P+](C([P+](C2CCCCC2)(C2CCCCC2)C2CCCCC2)C2C=CC=CC=2)(C2CCCCC2)C2CCCCC2)CC1.Cl[Ru]Cl>[CH2:1]([O:8][C:9]([N:10]1[CH2:16][CH:17]=[CH:18][CH2:13][CH2:12][CH2:11]1)=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 10539222Allyl-pent-4-enyl-carbamic acid benzyl ester

Product 1

HCID 106810412,3,4,7-Tetrahydro-azepine-1-carboxylic acid benzyl esterYield 56.4%

Reagents, catalysts & solvents 2

HCID 86306055bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

Allyl-pent-4-enyl-carbamic acid benzyl ester (15.5 g, 59.8 mmol) was dissolved in dichloromethane and bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride (1 g) was added. The mixture was refluxed under a nitrogen atmosphere until TLC analysis showed complete reaction. The solvent was evaporated under vacuum and the residue was purified by flash chromatography (ethyl acetate/hexane 1:9) to give 2,3,4,7-Tetrahydro-azepine-1-carboxylic acid benzyl ester (7.8 g).

Workup

  1. temperatureThe mixture was refluxed under a nitrogen atmosphere until TLC analysis
  2. customreaction
  3. customThe solvent was evaporated under vacuum
  4. customthe residue was purified by flash chromatography (ethyl acetate/hexane 1:9)

Sources & evidence

ORD record
ord-c856cdf8874f44769696a91ec6ff0fcb
Source dataset
uspto-grants-2007_03
Patent number
US07196099B2

Reaction notes

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