Isopropyl iodide → 7-Isopropyl-3-oxa-7,9-diaza-bicyclo[3.3.1]nonane
Reaction equation
C(OC([N:11]1[CH:16]2[CH2:17][NH:18][CH2:19][CH:12]1[CH2:13][O:14][CH2:15]2)=O)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].I[CH:27]([CH3:29])[CH3:28]>CN(C=O)C.CCOC(C)=O.CO.[Pd]>[CH:27]([N:18]1[CH2:17][CH:16]2[NH:11][CH:12]([CH2:13][O:14][CH2:15]2)[CH2:19]1)([CH3:29])[CH3:28]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 3-oxa-7,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic acid benzyl ester (Compound X) (100 mg, 0.33 mmol) in DMF (5 mL) was added K2CO3 (91 mg, 0.66 mmol) and 2-iodopropane (111 mg, 0.66 mmol). The reaction mixture was heated to 80° C. and stirred for 16 hours. The mixture was diluted with EtOAc (60 mL), and then washed with sat. NH4Cl, sat. NaHCO3 and brine (20 mL) respectively. The organic layer was dried over Na2SO4, and then concentrated to give the crude product which was dissolved in MeOH (20 mL). To the solution was added 10% Pd on carbon (20 mg). The mixture was stirred under one atmosphere pressure of H2 at room temperature. After the reaction was completed, the mixture was filtered and concentrated to give the crude 7-isopropyl-3-oxa-7,9-diaza-bicyclo[3.3.1]nonane (Compound AA) (32 mg, 57%) which was directly used for next step. MS: calc'd (MH+) 171, measured (MH+) 171.
Workup
- washwashed with sat. NH4Cl, sat. NaHCO3 and brine (20 mL) respectively
- dry with materialThe organic layer was dried over Na2SO4
- concentrationconcentrated
- customto give the crude product which
- stirringThe mixture was stirred under one atmosphere pressure of H2 at room temperature
- filtrationthe mixture was filtered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-bb2d72ad376c4942aba01062546f105c
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09266904B2
Reaction notes
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