(2R,3S)-benzyl 4-benzyl-2-methylmorpholine-3-carboxylate → (2R,3S)-2-methylmorpholine-3-carboxylic acid
Reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH3:14])[C@H:9]1[C:15]([O:17]CC1C=CC=CC=1)=[O:16])C1C=CC=CC=1>CO.[Pd]>[CH3:14][C@H:10]1[O:11][CH2:12][CH2:13][NH:8][C@@H:9]1[C:15]([OH:17])=[O:16]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
A mixture of (2R,3S)-benzyl 4-benzyl-2-methylmorpholine-3-carboxylate (10 g, 30.76 mmol) and Pd/C (10%, 1 g) in anhydrous methanol (100 mL) was stirred at 25° C. for 12 hours under H2. The mixture was filtered and the filtrate was concentrated in vacuo to give the title compound as a white solid (3.8 g, 85%). The compound was characterized by the following spectroscopic data:
Workup
- filtrationThe mixture was filtered
- concentrationthe filtrate was concentrated in vacuo
Sources & evidence
- ORD record
- ord-d327df40e32d40a9be3c56d518da26e8
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09340538B2
Reaction notes
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