Reaction #40785

Reaction equation

BH3.THF

NaOH

HCl

Tetrahydro-pyran-4,4-dicarbonitrile

→

yellow oil

Yield 62.1%

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

Yield 62.1%

Solvents

THF

THF

Conditions

Workup

1. 1
   Temperatureto warm to room temperature
2. 2
   TemperatureThe mixture was cooled in an ice bath
3. 3
   Temperatureto warm to room temperature
4. 4
   workup.STIRRINGstirred for 2 h
5. 5
   Extractionextracted three times with DCM
6. 6
   OtherThe aqueous layer was evaporated to dryness
7. 7
   workup.STIRRINGthe residue was stirred with CHCl3
8. 8
   Filtrationthe solids were filtered off
9. 9
   Otherthe organic phase was evaporated under reduced pressure

Procedure

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).

Source