HCID 86650568, compound → HCID 86650569, compound

HRID 1947696Notes

Reaction equation

HRID 1947696 reaction equation
[CH3:1][C:2]1([CH3:24])[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:5](/[CH:14]=[CH:15]/[CH:16]=[O:17])[C@@H:4]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:3]1>CC(C)=O.[Pd]>[CH3:1][C:2]1([CH3:24])[N:6]([C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8])[C@H:5]([CH2:14][CH2:15][CH:16]=[O:17])[C@@H:4]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:3]1

Participants

4

Reactant 1

HCID 86650568HCID 86650568, compound

Product 1

HCID 86650569HCID 86650569, compoundYield 58.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 180AcetoneSolvent

Procedure

To a solution of tert-butyl (4R,5R)-2,2-dimethyl-4-[(1E)-3-oxoprop-1-en-1-yl]-5-phenyl-1,3-oxazolidine-3-carboxylate (19.6 g, 59.1 mmol) (from Step A) in acetone (150 mL) was added 1.9 g of 10% Pd/C and the resulting suspension was stirred under a hydrogen balloon at ambient temperature for 24 h. The solid was filtered off on celite and the filtrate concentrated under vacuum. The residue was purified by flash chromatography on a Biotage Horizon® system (silica gel, 0 to 20% ethyl acetate in hexanes gradient then 20% ethyl acetate in hexanes) to afford 11.5 g (58%) of the title compound as a colorless oil. LC/MS 356.3 (M+23).

Workup

  1. filtrationThe solid was filtered off on celite
  2. concentrationthe filtrate concentrated under vacuum
  3. customThe residue was purified by flash chromatography on a Biotage Horizon® system (silica gel, 0 to 20% ethyl acetate in hexanes gradient

Sources & evidence

ORD record
ord-6b06c8af06c748b2967f41401eb6d202
Source dataset
uspto-grants-2013_03
Patent number
US08399480B2

Reaction notes

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