Sodium Chloride → HCID 71073858, compound

Participants

Reaction Conditions

Reaction Steps

The 4-(4-tert-butoxycarbonylaminopiperidin-1-yl)-dihydrocinnamic acid ethyl ester (68 g, 0.18 mol) obtained in Example 8(2) was dissolved in toluene (1 L) and cooled to −78° C. A diisobutylaluminum hydride-hexane solution (607 ml, 0.6 mol) was added dropwise. After stirring for 1.5 hours, methanol (10 ml) and a saturated sodium chloride aqueous solution (550 ml) were added, followed by stirring for 3 hours. The insoluble material was filtered with Celite. The solvent was evaporated from the filtrate, and the obtained residue was dissolved in methanol (500 ml) and THF (250 ml). Sodium borohydride (6.9 g, 0.18 mol) was added thereto at 0° C. After stirring for 1 hour, a saturated ammonium chloride aqueous solution was added thereto, followed by extraction with chloroform and drying over magnesium sulfate. After the desiccant was filtered off, the solvent was evaporated, thereby obtaining N-(4-(3-hydroxypropyl)phenyl)-4-tert-butoxycarbonylaminopiperidine (60 g, 98%).

Provenance & Evidence