tert-Butyl {(3S,5S)-5-(2,3-difluorophenyl)-2-oxo-1-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]piperidin-3-yl}carbamate → (3S,5S)-3-amino-5-(2,3-difluorophenyl)-1-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]piperidin-2-one
Reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:9]1[CH2:14][N:13]([CH2:15][C@H:16]([OH:21])[C:17]([F:20])([F:19])[F:18])[C:12](=[O:22])[C@@H:11]([NH:23]C(=O)OC(C)(C)C)[CH2:10]1>C(OCC)(=O)C>[NH2:23][C@H:11]1[CH2:10][C@@H:9]([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=2[F:1])[CH2:14][N:13]([CH2:15][C@H:16]([OH:21])[C:17]([F:20])([F:18])[F:19])[C:12]1=[O:22]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 23 °C
Procedure
A solution of tert-butyl {(3S,5S)-5-(2,3-difluorophenyl)-2-oxo-1-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]piperidin-3-yl}carbamate (39 mg, 0.089 mmol) in ethyl acetate (5 mL), pre-cooled to 0° C. was sparged with HCl gas for ˜1 min. The ice-bath was removed and the acidic solution was allowed to warm to 23° C. as stirring was continued for 2 h. The mixture was then concentrated to dryness to afford the title compound as a hydrochloride salt. MS: m/z=339.1 (M+1).
Workup
- customwas sparged with HCl gas for ˜1 min
- customThe ice-bath was removed
- concentrationThe mixture was then concentrated to dryness
Sources & evidence
- ORD record
- ord-1097b802c9a042509b179bb7ae233519
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08481556B2
Reaction notes
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