3-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (R)-(+)- → (R)-tert-butyl 4-(cyclopropyl(hydroxy)methyl)-2,2-dimethyloxazolidine-3-carboxylate

HRID 627241Notes

Reaction equation

HRID 627241 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].[CH:17]1([Mg]Br)[CH2:19][CH2:18]1>C1COCC1>[CH:17]1([CH:1]([OH:2])[C@H:3]2[CH2:7][O:6][C:5]([CH3:9])([CH3:8])[N:4]2[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 1787923-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (R)-(+)-HCID 178418630HCID 178418630, compound

Product 1

HCID 89851393(R)-tert-butyl 4-(cyclopropyl(hydroxy)methyl)-2,2-dimethyloxazolidine-3-carboxylateYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-tert-butyl 4-formyl-2,2-dimethyloxazolidine-3-carboxylate (Aldrich, 12.44 g, 54.26 mmol) in THF (150 mL) at −78° C. was added cyclopropylmagnesium bromide (217 mL, 108.52 mmol) dropwise. The reaction mixture was allowed to warm to room temperature and stir overnight. The reaction was quenched with water and diluted with ethyl acetate and brine. The resulting emulsion was filtered through celite and the layers separated. The organics were dried over magnesium sulfate, filtered and concentrated. Silica gel chromatography (0%-20% ethyl acetate/hexanes) afforded the title compound as a light yellow oil (12.47 g, 85%).

Workup

  1. customThe reaction was quenched with water
  2. additiondiluted with ethyl acetate and brine
  3. filtrationThe resulting emulsion was filtered through celite
  4. customthe layers separated
  5. dry with materialThe organics were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-1276d42fd0f24889a2b7195583168085
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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