HCID 10199020, compound → (1R,2S,4R)-N-BOC-1-AMINO-2-HYDROXYCYCLOPENTANE-4-CARBOXYLIC ACID METHYL ESTER

HRID 1358093Notes

Reaction equation

HRID 1358093 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.ClCCl>[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 2734528(1R,2S,4R)-N-BOC-1-AMINO-2-HYDROXYCYCLOPENTANE-4-CARBOXYLIC ACID METHYL ESTER

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

[(1,2-Bis(2R,5R)-2,5-dimethylphospholano)benzene](cyclooctadiene)rhodium(I) tetrafluoroborate (23 mg, 1 mol %) was added to a degassed solution of (3S,4R)-4-tert-butoxycarbonylamino-3-hydroxycyclopent-1-enecarboxylic acid methyl ester (1 g, 3.9 mmol) in methanol (5 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 14 h. The pressure was released and the bomb purged with nitrogen. Concentration of the reaction mixture gave a residue which was redissolved in dichloromethane (5 ml) Addition of silica (0.5 g) was stirring removed the catalyst from the reaction, and filtration and concentration of the organic solution gave the title compound as an off-white solid of 98% d.e. in quantitative yield.

Workup

  1. customafter purging with nitrogen
  2. customthe bomb purged with nitrogen
  3. customConcentration of the reaction mixture gave a residue which
  4. stirringwas stirring
  5. customremoved the catalyst
  6. customfrom the reaction, and filtration and concentration of the organic solution

Sources & evidence

ORD record
ord-a8694451fdd24b418ff3634eeaaa0200
Source dataset
uspto-grants-2003_07
Patent number
US06593489B1

Reaction notes

Loading…