Hydrochloride methanol → methyl (1S,2R)-1-amino-7-fluoroindane-2-carboxylate
Reaction equation
C([S@@]([NH:7][C@@H:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[F:17])[CH2:10][C@H:9]1[C:18]([O:20][C:21](C)(C)C)=[O:19])=O)(C)(C)C.Cl.CO>>[NH2:7][C@@H:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[F:17])[CH2:10][C@H:9]1[C:18]([O:20][CH3:21])=[O:19]Participants
Procedure
To 12 mg of tert-butyl (1S,2R)-1-{[(S)-tert-butylsulfinyl]amino}-7-fluoroindane-2-carboxylate (compound of Preparation Example 113a) was added 0.4 ml of a 10% hydrogen chloride/methanol solution, followed by stirring for 1 hour under ice-cooling. To the reaction mixture was added 1 ml of a 10% hydrogen chloride/methanol solution, followed by stirring at 50° C. for 6 hours. After leaving to be cooled, the solvent was evaporated under reduced pressure, and then to the obtained residue were added a saturated aqueous sodium hydrogen carbonate solution and ethyl acetate to carry out a layer separation operation. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain 6 mg of methyl (1S,2R)-1-amino-7-fluoroindane-2-carboxylate.
Workup
- temperaturecooling
- stirringby stirring at 50° C. for 6 hours
- customAfter leaving
- temperatureto be cooled
- customthe solvent was evaporated under reduced pressure
- additionto the obtained residue were added a saturated aqueous sodium hydrogen carbonate solution and ethyl acetate
- customa layer separation operation
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-1865849fd5ec4143ba993809e5d89b45
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09447090B2
Reaction notes
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