HCID 10199020, compound → methyl (1S,3R,4S)-3-{[(tert-butoxy)carbonyl]amino}-4-hydroxycyclopentane-1-carboxylate

HRID 1358094Notes

Reaction equation

HRID 1358094 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])[C@@H:7]([OH:18])[CH:6]=1)=[O:4]>CO.[Pd]>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:6][C@H:7]([OH:18])[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 10199020HCID 10199020, compound

Product 1

HCID 2734526methyl (1S,3R,4S)-3-{[(tert-butoxy)carbonyl]amino}-4-hydroxycyclopentane-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium-on-carbon (1 g, 10 wt %) was added under nitrogen to a solution of (3S,4R)-4-tert-butoxycarbonylamino-3-hydroxycyclopent-1-enecarboxylic acid methyl ester (70 g, 0.29 mol) in methanol (300 ml). The reaction mixture was transferred to a bomb, and, after purging with nitrogen and then hydrogen, a hydrogen pressure of 2 bar was applied and the reaction stirred for 14 h (periodically, additional hydrogen was added to the reaction, to reestablish and initial reaction pressure). The pressure was released and the bomb purged with nitrogen. The reaction mixture was cautiously filtered through Celite® and then concentrated to give the title compound as a syrup of 90% d.e. in quantitative yield.

Workup

  1. customafter purging with nitrogen
  2. additionwas added to the reaction
  3. custominitial reaction pressure)
  4. customthe bomb purged with nitrogen
  5. filtrationThe reaction mixture was cautiously filtered through Celite®
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b54882bde45f41d295fe73a136d83483
Source dataset
uspto-grants-2003_07
Patent number
US06593489B1

Reaction notes

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