반응 #46021

반응 방정식

Sodium borohydride

(2S,4R)-N-BOC-4-(t-butyldimethylsilyloxy)prolinaldehyde

→

(2S,4R)-N-BOC-4-(t-butyldimethylsilylhydroxy)prolinol

수율 105.0%

용매

MeOH

반응 조건

후처리

1. 1
   기타The reaction was quenched
2. 2
   workup.ADDITIONby adding sat. NaHCO3 (20 mL)
3. 3
   추출the resulting mixture was extracted with EtOAc (3×50 mL)
4. 4
   세척The EtOAc extracts were washed with brine (2×50 mL)
5. 5
   건조dried (Na2SO4)
6. 6
   기타The solvent was removed in vacuo

실험 절차

Sodium borohydride (227 mg, 6 mmol) was added at 0° C. to a stirred solution of (2S,4R)-N-BOC-4-(t-butyldimethylsilyloxy)prolinaldehyde (522 mg, 1.58 mmol) in MeOH (10 mL), and the mixture was stirred at rt for 3 h. The reaction was quenched by adding sat. NaHCO3 (20 mL), and the resulting mixture was extracted with EtOAc (3×50 mL). The EtOAc extracts were washed with brine (2×50 mL), and dried (Na2SO4). The solvent was removed in vacuo to give (2S,4R)-N-BOC-4-(t-butyldimethylsilylhydroxy)prolinol (550 mg).

출처