Cesium carbonate → Methyl cis(+/-)-3-(4-{[(benzyloxy)carbonyl]amino}-3-propoxypiperidin-1-yl)benzoate
Reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18](OC(C)(C)C)=O)[CH2:14][C@H:13]1[O:25][CH2:26][CH2:27][CH3:28])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(OCC)(=[O:32])C.C(O[C@H]1[C@@H](N[C:47](=O)[O:48][CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=C[CH:51]=2)CCNC1)CC.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:51]=[C:50]([CH:55]=[CH:54][CH:53]=2)[C:49]([O:48][CH3:47])=[O:32])[CH2:14][C@H:13]1[O:25][CH2:26][CH2:27][CH3:28])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
tert-Butyl cis(±)-4-{[(benzyloxy)carbonyl]amino}-3-propoxypiperidine-1-carboxylate obtained in Example (113e) (200 mg, 0.51 mmol) was dissolved in methanol (9 mL). A 4 N hydrochloric acid/ethyl acetate solution (6 mL) was added, and the mixture was stirred at room temperature for one hour. Following concentration under reduced pressure, the same operation as in Example (42a) was performed using the resulting benzyl cis(±)-[3-propoxypiperidin-4-yl]carbamate, methyl 3-bromo-5-benzoate (132 mg, 0.61 mmol), palladium acetate (11.4 mg, 0.05 mmol), BINAP (63.5 mg, 0.1 mmol) and cesium carbonate (498 mg, 1.53 mmol), to obtain 78 mg of the title compound as a pale yellow oily substance (36%).
Workup
- concentrationconcentration under reduced pressure
Sources & evidence
- ORD record
- ord-8c6fb9c184744363872cb9bc9bce1730
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08536197B2
Reaction notes
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