Lithium Hydroxide → HCID 86593061, compound
Reaction equation
[N:1]([C@H:4]1[C@@H:9]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8][CH2:7][C@@H:6]([C:18]([O:20]CC2C=CC=CC=2)=[O:19])[CH2:5]1)=[N+:2]=[N-:3].[OH-].[Li+]>O1CCCC1.O>[N:1]([C@H:4]1[C@@H:9]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:15])[CH3:16])=[O:12])[CH2:8][CH2:7][C@@H:6]([C:18]([OH:20])=[O:19])[CH2:5]1)=[N+:2]=[N-:3]Participants
Procedure
Benzyl (1R,3R,4S)-3-azido-4-(N-tert-butoxycarbonylamino)cyclohexane-1-carboxylate (3.5 g) was dissolved in tetrahydrofuran (130 ml) and water (16 ml), and lithium hydroxide (291 mg) was added under ice cooling. After 10 minutes, the mixture was heated to room temperature to continue stirring. After 20 hours, the reaction was stopped, the solvent was distilled off under reduced pressure, and the resultant residue was subjected to column chromatography on silica gel (methanol:dichloromethane=1:20) to obtain (1R,3R,4S)-3-azido-4-(N-tert-butoxycarbonylamino)cyclohexane-1-carboxylic acid (3.34 g) as a pale yellow oil. This product was dissolved in methanol (18 ml) and toluene (64 ml), trimethylsilyldiazomethane (2 M solution, 6.1 ml) was added under ice cooling, and the mixture was heated to room temperature and stirred. After 2 hours, the reaction was stopped, the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:4) to obtain the title compound (3.35 g) as a colorless oil.
Workup
- waitAfter 20 hours
- distillationthe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-7f3a88487452428b8bb0178dea36020b
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07935824B2
Reaction notes
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