Triacetoxyperiodinane → (R)-tert-butyl 4-(cyclopropanecarbonyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 627242Notes

Reaction equation

HRID 627242 reaction equation
[CH:1]1([CH:4]([OH:19])[C@H:5]2[CH2:9][O:8][C:7]([CH3:11])([CH3:10])[N:6]2[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.C(OCC)(=O)C>[CH:1]1([C:4]([C@H:5]2[CH2:9][O:8][C:7]([CH3:11])([CH3:10])[N:6]2[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[O:19])[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 89851393(R)-tert-butyl 4-(cyclopropyl(hydroxy)methyl)-2,2-dimethyloxazolidine-3-carboxylate2×

Product 1

HCID 89851368(R)-tert-butyl 4-(cyclopropanecarbonyl)-2,2-dimethyloxazolidine-3-carboxylateYield 90.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-tert-butyl 4-(cyclopropyl(hydroxy)methyl)-2,2-dimethyloxazolidine-3-carboxylate (Intermediate 230, 12.47 g, 45.95 mmol) in DCM (300 mL) at room temperature was added Dess-Martin periodinane (29.2 g, 68.93 mmol). The reaction mixture was stirred overnight then diluted with ethyl acetate and washed with saturated sodium bicarbonate. An emulsion formed and was filtered through celite. The layers were separated and the organics washed with brine. The organics were dried over magnesium sulfate, filtered and concentrated. Silica gel chromatography (0%-20% ethyl acetate/hexanes) afforded the title compound as a colorless oil (11.15 g, 90%).

Workup

  1. washwashed with saturated sodium bicarbonate
  2. customAn emulsion formed
  3. filtrationwas filtered through celite
  4. customThe layers were separated
  5. washthe organics washed with brine
  6. dry with materialThe organics were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-aaf102eb16724a6e9b4aa81ec41f9942
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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