Potassium Carbonate → (5S,6R)-3-Amino-6-methyl-1-(2,2,2-trifluoroethyl)-5-(2,3,5-trifluorophenyl)piperidin-2-one
Reaction equation
[CH3:1][C@H:2]1[N:7]([CH2:8][C:9]([F:12])([F:11])[F:10])[C:6](=[O:13])[CH:5]([NH:14]C(=O)OC(C)(C)C)[CH2:4][C@H:3]1[C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[C:24]([F:29])[C:23]=1[F:30].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>O>[NH2:14][CH:5]1[CH2:4][C@@H:3]([C:22]2[CH:27]=[C:26]([F:28])[CH:25]=[C:24]([F:29])[C:23]=2[F:30])[C@@H:2]([CH3:1])[N:7]([CH2:8][C:9]([F:12])([F:11])[F:10])[C:6]1=[O:13]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
To a solution of 47 (2.0 g, 4.5 mmol) in IPAC (20 mL) was added p-toluenesulfonic acid monohydrate (1.3 g, 6.8 mmol). The mixture was aged at 55° C. for 4 h. After the reaction was complete, the slurry was cooled in an ice bath to 5° C. and a solution of potassium carbonate (1.9 g, 13.6 mmol) in H2O (10 mL) was added. The aqueous layer (pH=10) was separated and the organic layer was washed with saturated aqueous NaHCO3, water and brine, in turns, and dried over Na2SO4. Concentration afforded 48 (1.3 g, 86% yield) as a 4:1 mixture of diastereomers.
Workup
- customThe aqueous layer (pH=10) was separated
- washthe organic layer was washed with saturated aqueous NaHCO3, water and brine, in turns
- dry with materialdried over Na2SO4
- concentrationConcentration
Sources & evidence
- ORD record
- ord-a631840ca57b4938bb3973c049d70281
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09174989B2
Reaction notes
Loading…