Reaktion #47471

Reaktionsgleichung

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

Ausbeute 93.2%

Lösungsmittel

tetrahydrofuran

isopropanol

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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]+.

Quelle