반응 #61640

반응 방정식

ammonium formate

trans-{4-[6-(1-benzyl-piperidin-4-ylamino)-9-cyclopent-2-enyl-9H-purin-2-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester

→

trans-{4-[9-cyclopent-2-enyl-6-(piperidin-4-ylamino)-9H-purin-2-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester

용매

water

water

methanol

반응 조건

후처리

1. 1
   온도heat at
2. 2
   온도a gentle reflux overnight
3. 3
   기타Remove the catalyst
4. 4
   여과by filtration through Celite®
5. 5
   농축concentrate the filtrate
6. 6
   workup.DISSOLUTIONDissolve the residue in DCM
7. 7
   추출extract with water
8. 8
   기타Remove the white precipitate
9. 9
   여과by filtration through a pad of Celite®
10. 10
    세척wash the filtrate with brine
11. 11
    건조dry over sodium sulfate
12. 12
    여과filter
13. 13
    농축Concentrate the filtrate
14. 14
    기타purify the residue on silica gel (50 g)

실험 절차

Add to a solution of trans-{4-[6-(1-benzyl-piperidin-4-ylamino)-9-cyclopent-2-enyl-9H-purin-2-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester (8c,1.0-mmol) in 40 mL of methanol, a suspension of Pd black (0.5 wt %) in a small amount of water. Then add a solution of ammonium formate (2.2 mmol) in 10 mL of water, and heat at a gentle reflux overnight. Remove the catalyst by filtration through Celite® and concentrate the filtrate. Dissolve the residue in DCM and extract with water. Remove the white precipitate by filtration through a pad of Celite®, wash the filtrate with brine, dry over sodium sulfate and filter. Concentrate the filtrate and purify the residue on silica gel (50 g) using DCM:methanol (4:1) to give trans-{4-[9-cyclopent-2-enyl-6-(piperidin-4-ylamino)-9H-purin-2-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester (9c.

출처