Sodium Hydroxide → Cyclohexanecarboxamide, 3-amino-4-hydroxy-N,N-dimethyl-, (1S,3R,4R)-
Reaction equation
[NH4+:1].[OH-:2].[OH-].[Na+].O[C@@H:6]1[C@@H:11](Br)[CH2:10][CH2:9][C@H:8]([C:13]([N:15]([CH3:17])[CH3:16])=[O:14])[CH2:7]1>>[NH2:1][C@H:6]1[C@H:11]([OH:2])[CH2:10][CH2:9][C@H:8]([C:13]([N:15]([CH3:17])[CH3:16])=[O:14])[CH2:7]1Participants
4
Conditions
- Temperature
- 40 °C
Procedure
A 28% ammonia aqueous solution (1563 ml) was added to an aqueous solution (500 ml) of (1S,3S,4S)-3-hydroxy-4-bromo-N,N-dimethylcyclohexanecarboxamide (274.5 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, 48% sodium hydroxide (67.3 ml) was added to the reaction mixture, and the obtained mixture was then concentrated to 500 ml to obtain the title compound (184.0 g, yield: 81%) in the form of an aqueous solution (572 g).
Workup
- stirringThereafter, the reaction solution was further stirred at room temperature for 6 hours
- concentrationthe obtained mixture was then concentrated to 500 ml
Sources & evidence
- ORD record
- ord-7455614a165e4479ba8ab94c4da646a9
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09447118B2
Reaction notes
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