Methanol → (3-(3,3-Dimethylbutyl)-3-azabicyclo[3.1.0]hexane-6-yl)methanamine
Reaction equation
[CH3:1][C:2]([CH3:15])([CH3:14])[CH2:3][CH2:4][N:5]1[CH2:10][CH:9]2[CH:7]([CH:8]2[C:11]([NH2:13])=O)[CH2:6]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].CO.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C(Cl)Cl.C(OCC)C>[CH3:1][C:2]([CH3:15])([CH3:14])[CH2:3][CH2:4][N:5]1[CH2:6][CH:7]2[CH:9]([CH:8]2[CH2:11][NH2:13])[CH2:10]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
The 3-(3,3-dimethylbutyl)-3-azabicyclo[3.1.0]hexane-6-carboxamide (170 mg, 0.808 mmol) prepared in Example 6 was dissolved in 7.42 mL of methylene chloride and 1 M lithium aluminum hydride (LAH; 3.23 mL, 3.23 mmol) dissolved in diethyl ether was added dropwise at 0° C. After stirring for 5 minutes, the mixture was heated to room temperature. 15 minutes later, the mixture was stirred for 23 hours at 55° C. under reflux. The completion of the reaction was confirmed by TLC (CH2Cl2:MeOH=10:1). After the reaction was completed, sodium sulfate hydrate was cautiously added at 0° C. The reaction mixture was filtered sequentially through Celite and anhydrous sodium sulfate, concentrated under reduced pressure and dried to obtain 130 mg (82.0%) of the target compound.
Workup
- additionwas added dropwise at 0° C
- stirring15 minutes later, the mixture was stirred for 23 hours at 55° C.
- temperatureunder reflux
- filtrationThe reaction mixture was filtered sequentially through Celite and anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customdried
Sources & evidence
- ORD record
- ord-e2881b16efa94dc2999a42cef89d949c
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08895602B1
Reaction notes
Loading…