반응 #47471

반응 방정식

sodium borohydride

water

hydrochloric acid

(S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid t-butyl ester

→

(R)-4-hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid t-butyl ester

수율 93.2%

용매

tetrahydrofuran

isopropanol

반응 조건

후처리

1. 1
   workup.ADDITIONAfter addition
2. 2
   workup.ADDITIONwas slowly added
3. 3
   추출extracted with ethyl acetate (3×30 mL)
4. 4
   세척The combined organic fractions were washed with a saturated sodium chloride solution
5. 5
   건조dried over magnesium sulfate

실험 절차

To an ice cold mixture of (S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid t-butyl ester (2.00 g, 8.72 mmol) in tetrahydrofuran (15 mL) and isopropanol (15 mL) was added sodium borohydride (0.99 g, 26.17 mmol). After addition was complete the mixture was stirred at 0° C. for 1 h. Upon completion of the reaction 1N aqueous hydrochloric acid (10 mL) was slowly added. The mixture was poured into water and extracted with ethyl acetate (3×30 mL). The combined organic fractions were washed with a saturated sodium chloride solution and dried over magnesium sulfate. The crude product obtained (R)-4-hydroxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid t-butyl ester (1.88 g, 93%) as a colorless oil and was used without further purification: LR-ES-MS m/z calculated for C11H21NO4 [M]+ 231, observed 232 [M+H]+.

출처