HCID 10692325, compound → HCID 10621099, compound

HRID 602469Notes

Reaction equation

HRID 602469 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@H:11](/[CH:21]=[CH:22]/[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>C(O)C.[Pd]>[Si:1]([O:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[C@H:11]([CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 10692325HCID 10692325, compound

Product 1

HCID 10621099HCID 10621099, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of tert-butyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-[(1E)-3-ethoxy-3-oxoprop-1-en-1-yl]pyrrolidine-1-carboxylate (1.37 g, 3.4 mmol, J. Antibiotics, 1997, 50, 567-585) in ethanol (30 mL) was added 10 wt. % palladium on carbon (140 mg). The resulting mixture was stirred under hydrogen (4 atom) at room temperature for 3 h. The mixture was filtered through a pad of Celite and the filter cake was washed with ethanol. The combined filtrate was concentrated to give 1.34 g (97%) of the title compound as a colorless oil.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. washthe filter cake was washed with ethanol
  3. concentrationThe combined filtrate was concentrated

Sources & evidence

ORD record
ord-f3a2cbbd08c64987ba4fdbfd348ece36
Source dataset
uspto-grants-2011_03
Patent number
US07906532B2

Reaction notes

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