反応 #40785

反応方程式

BH3.THF

NaOH

HCl

Tetrahydro-pyran-4,4-dicarbonitrile

→

yellow oil

収率 62.1%

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

収率 62.1%

溶媒

THF

THF

反応条件

後処理

1. 1
   温度to warm to room temperature
2. 2
   温度The mixture was cooled in an ice bath
3. 3
   温度to warm to room temperature
4. 4
   workup.STIRRINGstirred for 2 h
5. 5
   抽出extracted three times with DCM
6. 6
   その他The aqueous layer was evaporated to dryness
7. 7
   workup.STIRRINGthe residue was stirred with CHCl3
8. 8
   ろ過the solids were filtered off
9. 9
   その他the organic phase was evaporated under reduced pressure

実験手順

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).

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