반응 #9002

반응 방정식

sodium potassium tartrate

ester

2-(tert-butoxycarbonylamino-methyl)-oxazole-4-carboxylic acid methyl ester

DIBAL-H

→

(4-hydroxymethyl-oxazol-2-ylmethyl)-carbamic acid tert-butyl ester

수율 28.4%

용매

dichloromethane

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture was stirred rapidly for 30 minutes (until the aqueous and organic layers
2. 2
   기타were then separated
3. 3
   추출The aqueous layer was extracted twice with dichloromethane
4. 4
   건조The combined organic fractions were then dried over anhydrous sodium sulfate
5. 5
   농축concentrated
6. 6
   기타Purification by chromatography on silica gel (5% methanol in dichloromethane)

실험 절차

The ester (178 mg, 0.695 mmol) in 0° C. dichloromethane (8 mL) was treated with DIBAL-H (1 M in dichloromethane, 2.08 mL, 2.08 mmol). The mixture was then stirred at 0° C. for 2 hours before being treated with aqueous 5% sodium potassium tartrate (8 mL). The mixture was stirred rapidly for 30 minutes (until the aqueous and organic layers clarified), and the layers were then separated. The aqueous layer was extracted twice with dichloromethane. The combined organic fractions were then dried over anhydrous sodium sulfate and concentrated. Purification by chromatography on silica gel (5% methanol in dichloromethane) gave (4-hydroxymethyl-oxazol-2-ylmethyl)-carbamic acid tert-butyl ester as an oil (45 mg, 28%). 1H NMR (CDCl3) δ 1.40 (s, 9H), 4.43 (d, 2H, J=5.6 Hz), 4.56 (s, 2H), 5.37 (s, 1H), 7.54 (s, 1H).

출처