(R)-Tert-butyl 4-acetyl-2,2-dimethyloxazolidine-3-carboxylate → HCID 68714982, compound

HRID 1911521Notes

Reaction equation

HRID 1911521 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C:13](=[O:15])[CH3:14])[CH2:11][O:10][C:9]1([CH3:17])[CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:18]([Mg]Cl)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1COCC1>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C:13]([OH:15])([CH3:14])[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:11][O:10][C:9]1([CH3:16])[CH3:17])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 10977654(R)-Tert-butyl 4-acetyl-2,2-dimethyloxazolidine-3-carboxylateHCID 178418336HCID 178418336, compound

Product 1

HCID 68714982HCID 68714982, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (R)-4-acetyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (2.80 g, CAS 167102-63-8) in THF (40 ml) was cooled under an argon atmosphere to 0° C. and treated dropwise with benzylmagnesium chloride solution (1 M in diethylether, 34.5 ml). The reaction mixture was stirred at r.t. overnight, then quenched with saturated aqueous NH4Cl (50 ml) and extracted with EtOAc. The organic layer was washed with H2O and brine, dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (silica gel; gradient: cyclohexane ->cyclohexane/EtOAc 3:1) to give (R)-4-(1-hydroxy-1-methyl-2-phenyl-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (3.45 g, 89%) as off-white waxy solid.

Workup

  1. customquenched with saturated aqueous NH4Cl (50 ml)
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography (silica gel; gradient: cyclohexane ->cyclohexane/EtOAc 3:1)

Sources & evidence

ORD record
ord-b63b63a03c6247b786ea3d647a2914ca
Source dataset
uspto-grants-2013_12
Patent number
US08604061B2

Reaction notes

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