반응 #89164

반응 방정식

(−)-(2S,3R)-1-((benzyloxy)carbonyl)-3-methylpiperidine-2-carboxylic acid

BH3.THF

→

title compound

수율 92.3%

(2S,3R)-Benzyl 2-(Hydroxymethyl)-3-methylpiperidine-1-carboxylate

수율 92.3%

용매

THF

반응 조건

후처리

1. 1
   기타After this time, the reaction was quenched by the slow addition of ice cold water (10 mL)
2. 2
   workup.STIRRINGThe resulting mixture was stirred at rt for 30 min
3. 3
   추출extracted with EtOAc (3×100 mL)
4. 4
   건조The combined extracts were dried over anhydrous Na2SO4
5. 5
   여과filtered
6. 6
   농축concentrated under reduced pressure
7. 7
   기타The resulting residue was purified by flash column chromatography on silica gel eluting with 20% to 50% EtOAc/CH2Cl2

실험 절차

To a stirred solution of (−)-(2S,3R)-1-((benzyloxy)carbonyl)-3-methylpiperidine-2-carboxylic acid (6.05 g, 21.8 mmol) in anhydrous THF (80 mL) was added BH3.THF (1 M in THF, 43.6 mL, 43.6 mmol) dropwise over 10 min at rt under nitrogen. The reaction mixture was then stirred at rt for 46 h. After this time, the reaction was quenched by the slow addition of ice cold water (10 mL) followed by 2 N HCl (20 mL). The resulting mixture was stirred at rt for 30 min and then extracted with EtOAc (3×100 mL). The combined extracts were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography on silica gel eluting with 20% to 50% EtOAc/CH2Cl2 to afford the title compound as a colorless oil (5.30 g, 92%). ESI MS (M+H) 264.

출처