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 1436807Notes

Reaction equation

HRID 1436807 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 50 psi H2. 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. addition10% Palladium on carbon (0.14 g) was added
  3. filtrationThe mixture was filtered through celite
  4. washwashed with methylene chloride
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-afb7b0df2e1f48bebf763bfc8046652d
Source dataset
uspto-grants-2009_11
Patent number
US07618970B2

Reaction notes

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