Ammonium Hydroxide → Cyclohexanecarboxamide, 3-amino-4-hydroxy-N,N-dimethyl-, (1S,3R,4R)-
Reaction equation
[NH4+:1].[OH-:2].O[C@@H:4]1[C@@H:9](Br)[CH2:8][CH2:7][C@H:6]([C:11]([N:13]([CH3:15])[CH3:14])=[O:12])[CH2:5]1>>[NH2:1][C@H:4]1[C@H:9]([OH:2])[CH2:8][CH2:7][C@H:6]([C:11]([N:13]([CH3:15])[CH3:14])=[O:12])[CH2:5]1Participants
3
Conditions
- Temperature
- 40 °C
Procedure
A 28% ammonia aqueous solution (125 mL) was added to an aqueous solution (50 mL) of (1S,3S,4S)-3-hydroxy-4-bromo-N,N-dimethylcyclohexanecarboxamide (21.84 g), and the obtained solution was then heated to 40° C., followed by stirring the reaction solution for 8 hours. Thereafter, the reaction solution was further stirred at room temperature for 6 hours. Thereafter, the reaction mixture was concentrated to 50 mL to obtain 14.33 g of the title compound (yield: 79%) in the form of an aqueous solution (49 g).
Workup
- stirringThereafter, the reaction solution was further stirred at room temperature for 6 hours
- concentrationThereafter, the reaction mixture was concentrated to 50 mL
Sources & evidence
- ORD record
- ord-432ae0995ad142ad9b51355b662acaee
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09447118B2
Reaction notes
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