Water → iso-Propyl 7-benzyl-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate

HRID 2180013Notes

Reaction equation

HRID 2180013 reaction equation
[CH:1]([O:4][C:5](Cl)=[O:6])([CH3:3])[CH3:2].[OH-].[Na+].O.[CH2:11]([N:18]1[CH2:25][CH:24]2[CH2:26][CH:20]([CH2:21][NH:22][CH2:23]2)[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(Cl)Cl>[CH2:11]([N:18]1[CH2:19][CH:20]2[CH2:26][CH:24]([CH2:23][N:22]([C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[O:6])[CH2:21]2)[CH2:25]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7917Isopropyl chloroformateHCID 14798Sodium HydroxideHCID 130594823-Benzyl-3,7-diazabicyclo[3.3.1]nonane

Product 1

HCID 54513188iso-Propyl 7-benzyl-3,7-diazabicyclo[3.3.1]nonane-3-carboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

iso-Propylchloroformate (55 mmol) and concentrated NaOH (6.0 mL; 10 M) were added, along with 10 mL of water, to a solution of 3-benzyl-3,7-diazabicyclo[3.3.1]nonane (from step (ii) above; 10.8 g; 50 mmol) in CH2Cl2 (50 mL). The reaction mixture was stirred for 3 h and the phases separated. The organic phase was washed with H2O and brine, dried and concentrated to give the sub-title compound in 95% yield.

Workup

  1. customthe phases separated
  2. washThe organic phase was washed with H2O and brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-998ca1e7053847d7a2e38644c6f34ba4
Source dataset
uspto-grants-2005_05
Patent number
US06887881B1

Reaction notes

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