Methyl 2-[4-(methoxycarbonyl)(1,3-oxazolidin-3-yl)]-2-oxoacetate → Methyl 3-(3,3-dimethyl-2-oxopentanoyl)-1,3-oxazolidine-4-carboxylate

HRID 1250187Notes

Reaction equation

HRID 1250187 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][O:8][CH2:7][N:6]1[C:10](=[O:15])[C:11]([O:13]C)=O)=[O:4].[CH3:16][C:17]([Mg]Cl)([CH3:20])[CH2:18][CH3:19]>C1COCC1>[CH3:16][C:17]([CH3:20])([CH2:18][CH3:19])[C:11](=[O:13])[C:10]([N:6]1[CH:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:9][O:8][CH2:7]1)=[O:15]

Participants

4

Reactant 2

HCID 11085231Methyl 2-[4-(methoxycarbonyl)(1,3-oxazolidin-3-yl)]-2-oxoacetateHCID 178446075HCID 178446075, compound

Product 1

HCID 10956210Methyl 3-(3,3-dimethyl-2-oxopentanoyl)-1,3-oxazolidine-4-carboxylateYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-[4-(methoxycarbonyl)(1,3-oxazolidin-3-yl)]-2-oxoacetate (2) (0.84 g, 3.87 mM) in THF (50 ml) cooled to −78° C. was added 1,1-dimethylpropylmagnesium chloride (1M in THF, 8 ml, 8 mM). After 3 hrs. at −78° C. the mixture was quenched with saturated NH4Cl (50 ml) and extracted with ethyl acetate (100 ml). The organic layer separated, washed with brine (100 ml), dried with anhydrous magnesium sulfate, filtered and evaporated. The resulting pale yellow oil was flash chromatographed eluting with 20% EtOAc/hexane. A clear oil (3) (0.61 g, 61%) was obtained.

Workup

  1. customat −78° C. the mixture was quenched with saturated NH4Cl (50 ml)
  2. extractionextracted with ethyl acetate (100 ml)
  3. customThe organic layer separated
  4. washwashed with brine (100 ml)
  5. dry with materialdried with anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customchromatographed
  9. washeluting with 20% EtOAc/hexane

Sources & evidence

ORD record
ord-a41447246e914dfbbeb7d400682dfb02
Source dataset
uspto-grants-2002_01
Patent number
US06337340B1

Reaction notes

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