Reacción #577251

ord-e730deec6b04425fbbdeee2dcb321a6a

Ecuación de reacción

CC(C)(C)OC(=O)N1C(CCc2ccc(OCc3ccccc3)cc2)(COC(=O)c2ccccc2[N+](=O)[O-])COC1(C)C
4-[2-(4-benzyloxy-phenyl)-ethyl]-2,2-dimethyl-4-(2-nitro-benzoyloxymethyl)-oxazolidine-3-carboxylic acid tert-butyl ester
O=C([O-])[O-].[K+].[K+]
K2CO3
CC(C)(C)OC(=O)N1C(CO)(CCc2ccc(OCc3ccccc3)cc2)COC1(C)C
4-[2-(4-benzyloxy-phenyl)-ethyl]-4-hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
Rendimiento 88.8%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    ConcentraciónThe reaction mixture is concentrated to dryness

Procedimiento

To a solution of 4-[2-(4-benzyloxy-phenyl)-ethyl]-2,2-dimethyl-4-(2-nitro-benzoyloxymethyl)-oxazolidine-3-carboxylic acid tert-butyl ester (80 mg, 0.13 mmol) in methanol (1 ml) and THF (1 ml) is added K2CO3 (1.5 mg, 0.076 eq), the reaction mixture is stirred overnight at room temperature. The reaction mixture is concentrated to dryness and 4-[2-(4-benzyloxy-phenyl)-ethyl]-4-hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (51 mg, 85%) is isolated as a white solid after flash chromatography (Ethyl acetate/Hexane (1/4)).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07528120B2uspto-grants-2009_05