Dimethylformamide → (R)-2,2-dimethyl-4-(3-nitro-pyrazol-1-ylmethyl)-oxazolidine-3-carboxylic acid t-butyl ester

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Reaction Conditions

Reaction Steps

To a stirred mixture of (S)-2,2-dimethyl-4-(toluene-4-sulfonyloxymethyl-oxazolidine-3-carboxylic acid t-butyl ester (2.20 g, 5.71 mmol) in N,N-dimethylformamide (10 mL) was added potassium carbonate (0.93 g, 6.73 mmol) and 3-nitro-1H-pyrazole (prepared as in Example 5, 0.59 mg, 5.20 mmol). After addition was complete the mixture was stirred at 60° C. for 18 h. The reaction mixture was diluted with ethyl acetate, washed with water followed by a saturated sodium chloride solution and dried over magnesium sulfate. The organic layer was concentrated, and the crude product was purified by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 40 g; 0% to 100% ethyl acetate/hexanes) to afford (R)-2,2-dimethyl-4-(3-nitro-pyrazol-1-ylmethyl)-oxazolidine-3-carboxylic acid t-butyl ester (1.21 g, 65%) as a colorless oil: LR-ES-MS m/z calculated for C14H22N4O5 [M]+ 326, observed 327 [M+H]+.

Provenance & Evidence