3-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (R)-(+)- → HCID 15382944, compound

HRID 627202Notes

Reaction equation

HRID 627202 reaction equation
[CH:1]([C@H:3]1[CH2:7][O:6][C:5]([CH3:9])([CH3:8])[N:4]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:2].[CH3:17][Mg]Br>C1COCC1>[OH:2][CH:1]([C@H:3]1[CH2:7][O:6][C:5]([CH3:9])([CH3:8])[N:4]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH3:17]

Participants

4

Reactant 2

HCID 1787923-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (R)-(+)-2×HCID 178418573HCID 178418573, compound2×

Product 1

HCID 15382944HCID 15382944, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-tert-butyl 4-formyl-2,2-dimethyloxazolidine-3-carboxylate (Intermediate 182, 10.18 g, 44.40 mmol) in THF (188 mL) at −78° C. was added methyl magnesium bromide (16.28 mL, 48.84 mmol) dropwise. The reaction mixture was allowed to warm to room temperature and stir overnight under nitrogen atmosphere. Re-cooled reaction mixture to −78° C. and added dropwise additional 13 mL (0.9 eq, to bring total to 2 eq) of methyl magnesium bromide. Allowed reaction mixture to stir at −78° C. for 3 hours and warm to room temperature. The reaction mixture was quenched with water and diluted with ethyl acetate saturated sodium chloride (brine). The resulting emulsion was filtered thru celite and the layers separated. The organic layers were dried over magnesium sulfate, filtered, concentrated. Silica gel chromatography (0%-20% ethyl acetate/hexanes) afforded the title compound as a colorless oily solid (8.42 g, 77%).

Workup

  1. customRe-cooled reaction mixture to −78° C.
  2. stirringAllowed reaction mixture to stir at −78° C. for 3 hours
  3. temperaturewarm to room temperature
  4. customThe reaction mixture was quenched with water
  5. additiondiluted with ethyl acetate saturated sodium chloride (brine)
  6. filtrationThe resulting emulsion was filtered thru celite
  7. customthe layers separated
  8. dry with materialThe organic layers were dried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-d5105c2e58ec4c43a84c8fb3fd691a83
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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