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

HRID 1596434

Reaction equation

HRID 1596434 reaction equation
[OH-].[Na+].O.[CH:4]([O:7][C:8](Cl)=[O:9])([CH3:6])[CH3:5].[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:8]([O:7][CH:4]([CH3:6])[CH3:5])=[O:9])[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

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

Workup

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

Sources & evidence

ORD record
ord-cbd8160ffd954c33a551837f092a1e88
Source dataset
uspto-grants-2001_09
Patent number
US06291475B1

Linked notes

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