반응 #40785

반응 방정식

BH3.THF

NaOH

HCl

Tetrahydro-pyran-4,4-dicarbonitrile

→

yellow oil

수율 62.1%

C-(4-Aminomethyl-tetrahydro-pyran-4-yl)-methylamine

수율 62.1%

용매

THF

THF

반응 조건

후처리

1. 1
   온도to warm to room temperature
2. 2
   온도The mixture was cooled in an ice bath
3. 3
   온도to warm to room temperature
4. 4
   workup.STIRRINGstirred for 2 h
5. 5
   추출extracted three times with DCM
6. 6
   기타The aqueous layer was evaporated to dryness
7. 7
   workup.STIRRINGthe residue was stirred with CHCl3
8. 8
   여과the solids were filtered off
9. 9
   기타the organic phase was evaporated under reduced pressure

실험 절차

Tetrahydro-pyran-4,4-dicarbonitrile (1.52 g) was dissolved in dry THF (25 mL) and cooled to −10° C. To this solution, BH3.THF (56 mL of an 1M solution in THF, 5 equiv.) was added dropwise, the mixture was allowed to warm to room temperature, and subsequently stirred at 60° C. for 6 h. The mixture was cooled in an ice bath, and HCl (24.2 mL of a 6M aqueous solution, 13 equiv.) was added. The mixture was allowed to warm to room temperature and stirred for 2 h. The mixture was neutralized with 2M aqueous NaOH and extracted three times with DCM. The aqueous layer was evaporated to dryness, the residue was stirred with CHCl3, the solids were filtered off and the organic phase was evaporated under reduced pressure to yield 1.0 g (62%) of a yellow oil. 1H NMR (400 MHz, CDCl3) δ 1.46 (t, 4H), 2.74 (s, 4H), 3.67 (t, 4H).

출처