methyl (4S)-4-{[(tert-butoxy)carbonyl]amino}cyclopent-1-ene-1-carboxylate → ST50825900

HRID 1358096Notes

Reaction equation

HRID 1358096 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH2:9][C@@H:8]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH:6]=1)=[O:4]>CO.ClCCl>[CH3:1][O:2][C:3]([C@H:5]1[CH2:6][CH2:7][C@H:8]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9]1)=[O:4]

Participants

4

Reactant 1

HCID 10490292methyl (4S)-4-{[(tert-butoxy)carbonyl]amino}cyclopent-1-ene-1-carboxylate

Product 1

HCID 2734531ST50825900

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

((1,2-Bis(2R,5R)-2,5-dimethylphospholano)ethane)(cyclooctadiene)rhodium(I) trifluoromethanesulfonate (179 mg, 0.1 mol %) was added to a degassed solution of (4S)-4-tert-butoxycarbonylaminocyclopent-1-enecarboxylic acid methyl ester (70 g, 0.29 mol) in methanol (350 ml). The reaction mixture was transferred to a bomb and after purging with nitrogen and then hydrogen, a hydrogen pressure of 5 bar was applied and the reaction stirred for 62 h. The pressure was released and the bomb purged with nitrogen. Concentration of the reaction mixture gave a residue which was redissolved in dichloromethane (300 ml). Addition of silica (20 g) with stirring removed the catalyst from the reaction and filtration and concentration of the organic solution gave crude product as a yellow oil that solidified on standing (92% d.e.; measured by gc analysis). Crystallisation from tert-butylmethylether and heptane gave the title compound as colourless needles of 97% d.e. (63 g, 89%).

Workup

  1. customafter purging with nitrogen
  2. customthe bomb purged with nitrogen
  3. customConcentration of the reaction mixture gave a residue which
  4. additionAddition of silica (20 g)
  5. stirringwith stirring
  6. customremoved the catalyst
  7. customfrom the reaction and filtration and concentration of the organic solution
  8. customgave crude product as a yellow oil that
  9. customCrystallisation from tert-butylmethylether and heptane

Sources & evidence

ORD record
ord-1798494edd6e448798eb1d48f031a5e3
Source dataset
uspto-grants-2003_07
Patent number
US06593489B1

Reaction notes

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