HCID 10692325, compound → HCID 10621099, compound

HRID 225959Notes

Reaction equation

HRID 225959 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(OCC)(=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 80,136.602%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of tert-butyl (2S,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-[(1E)-3-ethoxy-3-oxoprop-1-en-1-yl]pyrrolidine-1-carboxylate (35 g, 0.087 mmol)) and Pd/C (3.5 g) in ethyl acetate (400 ml) was hydrogenated under a pressure of 80 psi for 2 h. The reaction mixture was filtered off and filtrate concentrated under vacuum to give tert-butyl (2R,4R)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(3-ethoxy-3-oxopropyl)pyrrolidine-1-carboxylate (28 g) as a liquid. Yield: 80%

Workup

  1. filtrationThe reaction mixture was filtered off
  2. concentrationfiltrate concentrated under vacuum

Sources & evidence

ORD record
ord-7840e54a602c4df08186d9481a7a50f8
Source dataset
uspto-grants-2009_07
Patent number
US07557136B2

Reaction notes

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