Ethyl 3-(Cyanomethyl)-3-azatricyclo[5.2.1.02,6]deca-2(6),4-diene-4-carboxylate → Ethyl 3-(2-Aminoethyl)-3-azatricyclo[5.2.1.02,6]deca-2(6),4-diene-4-carboxylate

HRID 592733Notes

Reaction equation

HRID 592733 reaction equation
[C:1]([CH2:3][N:4]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][C:10]2[CH:9]3[CH2:18][CH:6]([CH2:7][CH2:8]3)[C:5]1=2)#[N:2]>CO.[Ni]>[NH2:2][CH2:1][CH2:3][N:4]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][C:10]2[CH:9]3[CH2:18][CH:6]([CH2:7][CH2:8]3)[C:5]1=2

Participants

4

Reactant 1

HCID 58043774Ethyl 3-(Cyanomethyl)-3-azatricyclo[5.2.1.02,6]deca-2(6),4-diene-4-carboxylate

Product 1

HCID 58044168Ethyl 3-(2-Aminoethyl)-3-azatricyclo[5.2.1.02,6]deca-2(6),4-diene-4-carboxylateYield 50.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A suspension of 167d (4.0 g, 16 mmol) and Raney Ni (400 mg) in methanol (60 mL) was hydrogenated in a Parr apparatus at 50 psi overnight. The mixture was filtered through a pad of CELITE® and the filtrate was concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 20:1 methylene chloride/methanol to afford 167e as a yellow solid (2.0 g, 50%). MS: [M+H]+ 249.

Workup

  1. customwas hydrogenated in a Parr apparatus at 50 psi overnight
  2. filtrationThe mixture was filtered through a pad of CELITE®
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica-gel column chromatography
  5. washeluting with 20:1 methylene chloride/methanol

Sources & evidence

ORD record
ord-50840b51868a4f46bb8bf5b8bb3cd263
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

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