Water → (4-(Methoxymethyl)cyclohexyl)methanamine
Reaction equation
[CH3:1][O:2][CH2:3][CH:4]1[CH2:9][CH2:8][CH:7]([C:10]#[N:11])[CH2:6][CH2:5]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].O>O1CCCC1>[CH3:1][O:2][CH2:3][CH:4]1[CH2:9][CH2:8][CH:7]([CH2:10][NH2:11])[CH2:6][CH2:5]1Participants
6
Procedure
To a solution of EXAMPLE 454D (460 mg) in tetrahydrofuran (15 mL) was added 2M lithium aluminum hydride in tetrahydrofuran (2.252 mL) slowly. The reaction mixture was stirred at room temperature for 1 hour, refluxed for 1 hour and cooled. Sodium hydroxide (2 ml of 2M solution) and water (5 mL) was added. The solid was filtered off and washed with ether. The filtrate was concentrated. The residue was mixed with dichloromethane (50 mL) and the resulting mixture was dried over Na2CO3, filtered, and concentrated to provide the title compound.
Workup
- temperaturerefluxed for 1 hour
- temperaturecooled
- filtrationThe solid was filtered off
- washwashed with ether
- concentrationThe filtrate was concentrated
- additionThe residue was mixed with dichloromethane (50 mL)
- dry with materialthe resulting mixture was dried over Na2CO3
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-b16a953cc600465c8b370b363fd502ff
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09029404B2
Reaction notes
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