Acetonitrile → Tert-butyl 8-[2-(4-cyanophenoxy)ethyl]-3,8-diazabicyclo[3.2.1]octane-3-carboxylate

HRID 1743720Notes

Reaction equation

HRID 1743720 reaction equation
Cl.[CH:2]12[NH:9][CH:6]([CH2:7][CH2:8]1)[CH2:5][N:4]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:3]2.C(#N)C.Br[CH2:21][CH2:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][CH:25]=1.C([O-])([O-])=O.[K+].[K+]>O.C(Cl)(Cl)Cl>[C:28]([C:27]1[CH:30]=[CH:31][C:24]([O:23][CH2:22][CH2:21][N:9]2[CH:6]3[CH2:7][CH2:8][CH:2]2[CH2:3][N:4]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5]3)=[CH:25][CH:26]=1)#[N:29]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 24522124-(2-Bromoethoxy)benzonitrileHCID 22235404tert-Butyl 3,8-diazabicyclo[3.2.1]octane-3-carboxylate hydrochloride

Product 1

HCID 22235539Tert-butyl 8-[2-(4-cyanophenoxy)ethyl]-3,8-diazabicyclo[3.2.1]octane-3-carboxylate

Reagents, catalysts & solvents 1

HCID 22418719Chloroform waterSolvent

Procedure

tert-Butyl 3,8-diazabicyclo[3.2.1]octane-3-carboxylate hydrochloride (1.36 g, 5.5 mmol; see Preparation A) was dissolved in H2O/CHCl3/saturated K2CO3 solution (40:40:5) and the resulting mixture was shaken. The phases were separated, dried and evaporated giving 1.1 g (100%), of the free base. Acetonitrile (100 mL), 4-(2-bromoethoxy)benzonitrile (1.49 g, 6.6 mmol; from step (a) above) and K2CO3 (2.4 g, 17.5 mmol) were added. The mixture was stirred at 70° C. for 24 h, the solids were filtered off and the residue evaporated and purified by chromatography on silica, eluting with CHCl3:MeOH (95:5), to give 1.5 g (4.3 mmol) of the sub-title compound.

Workup

  1. customPreparation A)
  2. customThe phases were separated
  3. customdried
  4. customevaporated
  5. customgiving 1.1 g (100%)
  6. stirringThe mixture was stirred at 70° C. for 24 h
  7. filtrationthe solids were filtered off
  8. customthe residue evaporated
  9. custompurified by chromatography on silica
  10. washeluting with CHCl3:MeOH (95:5)

Sources & evidence

ORD record
ord-e2f326d3fbe9491182119a7b49a65b55
Source dataset
uspto-grants-2006_03
Patent number
US07012074B2

Reaction notes

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