Water → rac-(1R,2R)-2-(methylamino)cyclohexan-1-ol
Reaction equation
C(O[C:6](=O)[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[OH:14])(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[CH3:6][NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[OH:14]Participants
6
Procedure
3.51 g racemic trans-(2-hydroxy-cyclohexyl)-carbamic acid tert-butyl ester were added to a suspension of 3.09 g lithium aluminium hydride in THF. The reaction mixture was heated at reflux over night. After that time subsequently 3.1 ml water, 3.1 ml sodium hydroxide solution (2M) and 3.1 ml water were added. The mixture was then stirred for 45 minutes and then filtered through celite. The celite was washed with EtOAc. The solvent was evaporated.
Workup
- temperatureThe reaction mixture was heated
- temperatureat reflux over night
- filtrationfiltered through celite
- washThe celite was washed with EtOAc
- customThe solvent was evaporated
Sources & evidence
- ORD record
- ord-9f9e80c4270e41e28f4c7d270229b3a1
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08754079B2
Reaction notes
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