Hydrogen chloride-ethyl acetate → Benzyl cis(+/-)-[3-methoxypiperidin-4-yl]carbamate
Reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][C@H:13]1[O:25][CH3:26])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(OCC)(=O)C>CO>[CH3:26][O:25][C@H:13]1[C@@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:17][CH2:16][NH:15][CH2:14]1Participants
4
Procedure
tert-Butyl cis(±)-4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidine-1-carboxylate obtained in Example (40a) (4.28 g, 11.7 mmol) was dissolved in methanol (20 mL). A 4 N hydrochloric acid/ethyl acetate solution (60 mL) was added, and the mixture was stirred at room temperature for 40 minutes. The reaction solution was concentrated under reduced pressure and then saturated aqueous sodium bicarbonate solution was added, followed by extraction with THF. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting compound was used for the next reaction without purification.