반응 #534973

반응 방정식

potassium carbonate

1,1-dimethylethyl 4-piperidinylcarbamate

tetrahydro-4H-pyran-4-one

DCM

sodium triacetoxyborohydride

→

title product

1-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine, dihydrochloride

용매

brine

Water

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture was stirred for 10 minutes at about 25° C.
2. 2
   기타the layers were separated
3. 3
   세척the organic layer washed with saturated brine (3×214 ml)
4. 4
   건조After drying over anhydrous sodium sulphate
5. 5
   농축the organic layer was concentrated
6. 6
   workup.ADDITIONthe residue was treated with 100 ml isopropanol
7. 7
   온도The residue was slowly heated
8. 8
   온도to reflux with 11% HCl in isopropanol (200 ml) for 2 hours
9. 9
   온도then cooled to about 25° C
10. 10
    여과The solid was filtered
11. 11
    세척slurry washed with diethyl ether (100 ml)
12. 12
    기타dried under high vacuum

실험 절차

To a solution of 1,1-dimethylethyl 4-piperidinylcarbamate (50 g) was added tetrahydro-4H-pyran-4-one (35.75 g) in dry DCM (1000 ml), then was added sodium triacetoxyborohydride (141 g) portion wise over 10 minutes at about 25° C. The mixture was stirred under nitrogen for about 30 hours, then cooled to 0° C. Water (107 ml) was added portion wise in 20 minutes, followed by saturated aqueous potassium carbonate (178 ml) and saturated brine (178 g in 178 ml). The mixture was stirred for 10 minutes at about 25° C., then the layers were separated and the organic layer washed with saturated brine (3×214 ml). After drying over anhydrous sodium sulphate, the organic layer was concentrated and the residue was treated with 100 ml isopropanol and reconcentrated. The residue was slowly heated to reflux with 11% HCl in isopropanol (200 ml) for 2 hours then cooled to about 25° C. The solid was filtered, and slurry washed with diethyl ether (100 ml), then dried under high vacuum to give the title product (43 g).

출처