Methyl (4S)-4-[(tert-butoxycarbonyl)amino]-1-(1-hydroxy-1-methylethyl)cyclopent-2-ene-1-carboxylate → methyl (3S)-3-[(tert-butoxycarbonyl)amino]-1-(1-hydroxy-1-methylethyl)cyclopentanecarboxylate

HRID 1261683Notes

Reaction equation

HRID 1261683 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][C:12]([C:18]([OH:21])([CH3:20])[CH3:19])([C:14]([O:16][CH3:17])=[O:15])[CH:11]=[CH:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:10][CH2:11][C:12]([C:18]([OH:21])([CH3:20])[CH3:19])([C:14]([O:16][CH3:17])=[O:15])[CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 86602445Methyl (4S)-4-[(tert-butoxycarbonyl)amino]-1-(1-hydroxy-1-methylethyl)cyclopent-2-ene-1-carboxylate

Product 1

HCID 86602446methyl (3S)-3-[(tert-butoxycarbonyl)amino]-1-(1-hydroxy-1-methylethyl)cyclopentanecarboxylateYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl (4S)-4-[(tert-butoxycarbonyl)amino]-1-(1-hydroxy-1-methylethyl)cyclopent-2-ene-1-carboxylate (1.4 g, 4.7 mmol) was dissolved in ethanol (30 mL) in a Parr flask and purged with N2. 10% Palladium on carbon (0.14 g; was added and the mixture was shaken overnight under nitrogen at 50 psi. The mixture was filtered through celite, washed with methylene chloride and concentrated to give the desired product (1.06 g, 86%).

Workup

  1. custompurged with N2
  2. additionwas added
  3. filtrationThe mixture was filtered through celite
  4. washwashed with methylene chloride
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7a821a7478ea4fc0aeac3dd80bb642dc
Source dataset
uspto-grants-2013_06
Patent number
US08470827B2

Reaction notes

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