Racemic methyl-3-azido-2-hydroxy-1-methyl-cyclohexane-carboxylate → Methyl-3-amino-2-hydroxy-1-methyl-cyclohexanecarboxylate
Reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH3:15])[CH2:10][CH2:9][CH2:8][CH:7]([N:11]=[N+]=[N-])[CH:6]1[OH:14])=[O:4]>CO.CC(O)=O.[Pd]>[CH3:1][O:2][C:3]([C:5]1([CH3:15])[CH2:10][CH2:9][CH2:8][CH:7]([NH2:11])[CH:6]1[OH:14])=[O:4]Participants
5
Procedure
A solution of racemic methyl-3-azido-2-hydroxy-1-methyl-cyclohexane-carboxylate, 66c, (0.90 g, 4.22 mmol) in a mixture of MeOH (50 mL) and AcOH (10 mL) was stirred under a hydrogen atmosphere (balloon) with the presence of palladium (0.50 g, 0.47 mmol) overnight at room temperature. The mixture was filtered through a celite bed and washed with MeOH. The combined filtrates were evaporated to provide methyl-3-amino-2-hydroxy-1-methyl-cyclohexanecarboxylate as a oil. Et2O was added and the resulted acetic acid salt was stirred for 0.5 hour and was then filtered to give 1.0 g of racemic methyl-3-amino-2-hydroxy-1-methyl-cyclohexanecarboxylate acetic acid salt as a white solid.
Workup
- filtrationThe mixture was filtered through a celite bed
- washwashed with MeOH
- customThe combined filtrates were evaporated
Sources & evidence
- ORD record
- ord-7a76e2cc3f264b1bbdb92f3c1c13a67b
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09345708B2
Reaction notes
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