反応 #160707

反応方程式

Benzoic acid

(3R,5R)-benzyl 3-(tert-butyldimethylsilyloxy)-5-hydroxypiperidine-1-carboxylate

triphenylphosphine

di-tert-butyl azodicarboxylate

→

(3S,5R)-benzyl 3-(benzoyloxy)-5-(tert-butyl-dimethylsilyloxy)piperidine-1-carboxylate

収率 77.0%

溶媒

THF

THF

反応条件

後処理

1. 1
   workup.STIRRINGstirred for 20 minutes at 0° C
2. 2
   温度to slowly warm to rt
3. 3
   濃縮After 16 hours the reaction mixture was concentrated in vacuo
4. 4
   workup.ADDITIONthen diluted with EtOAc
5. 5
   洗浄washed with water
6. 6
   乾燥The organic layer was dried with Na2SO4
7. 7
   ろ過filtered
8. 8
   濃縮concentrated in vacuo
9. 9
   その他The crude residue was purified by flash chromatography (EtOAc:hexanes=1:8)

実験手順

To a stirring 0° C. solution of triphenylphosphine (1.2 equiv) in 23 mL of THF was added di-tert-butyl azodicarboxylate (1.2 equiv). The mixture was stirred at 0° C. for 10 minutes. Then a solution of (3R,5R)-benzyl 3-(tert-butyldimethylsilyloxy)-5-hydroxypiperidine-1-carboxylate (1.0 equiv) in 11 mL of THF was added and stirred for 20 minutes at 0° C. Benzoic acid (1.2 equiv) was then added and the reaction mixture was allowed to slowly warm to rt. After 16 hours the reaction mixture was concentrated in vacuo then diluted with EtOAc and washed with water then brine. The organic layer was dried with Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography (EtOAc:hexanes=1:8) to yield (3S,5R)-benzyl 3-(benzoyloxy)-5-(tert-butyl-dimethylsilyloxy)piperidine-1-carboxylate (77%). LC/MS (m/z): 470.2 (MH+), HPLC Rt=6.05 min.

出典