Sodium Hydroxide → HCID 90015970, Verbindung
Reaktionsgleichung
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2([C:21]([O:23]CC)=[O:22])[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH:5]=[CH:4][N:3]=1.[OH-].[Na+]>C(O)C>[C:17]([O:16][C:14]([N:11]1[CH2:12][CH2:13][C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[CH:7]=2)([C:21]([OH:23])=[O:22])[CH2:9][CH2:10]1)=[O:15])([CH3:20])([CH3:18])[CH3:19]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a mixture of the compound 1-tert-butyl 4-ethyl 4-(2-chloropyridin-4-yl)piperidine-1,4-dicarboxylate (50 g, 0.14 mols, 1 equiv.) in ethanol (75 mL) was added 500 mL of a 10% solution of NaOH. The mixture was refluxed for 2 h. The reaction was monitored by TLC (ethyl acetate/petroleum ether; 1/5), cooled, concentrated to a half of the primary volume and extracted with methyltertiarybutyl ether (3×150 mL). The aqueous layer was acidified with 3M hydrochloric acid to pH=4 and extracted with dichloromethane (2×350 mL). The combined organic layers were dried over anhydrous sodium sulfate. The organic was concentrated to give crude product 1-(tert-butoxycarbonyl)-4-(2-chloropyridin-4-yl)piperidine-4-carboxylic acid (42 g, 91% crude). The crude was used as is in Step C.