Water → 1-(Benzyloxycarbonyl)-4-phenylpiperidine-4-carboxylic acid

HRID 355464

Reaktionsgleichung

C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:12]([C:15]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)([OH:14])=[O:13].[OH-].[Na+].O.Cl[C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32]>CC(C)=O>[CH2:34]([O:33][C:31]([N:18]1[CH2:17][CH2:16][C:15]([C:12]([OH:14])=[O:13])([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:20][CH2:19]1)=[O:32])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Komponenten

Reaktionsbedingungen

Temperatur: 5 °C

Versuchsvorschrift

A mixture of 37.7 g of 4-carboxy-4-phenylpiperidine p-toluenesulphonate, 53.3 g of 30% aqueous NaOH solution and 250 ml of water is cooled to 5° C. A solution of 18 g of benzyl chloroformate in 60 ml of acetone is added rapidly at 5° C., and the mixture is left stirring overnight while allowing the temperature to rise to RT. The reaction mixture is washed twice with ether and, after settling has taken place, the aqueous phase is separated and acidified to pH 1 by adding concentrated HCl and then 2N HCl. The precipitate formed is drained, dried, taken up in ether and drained again. 30.6 g of the expected product are obtained, m.p.=142°-144° C.

Aufarbeitung

waitthe mixture is left
customto rise to RT
washThe reaction mixture is washed twice with ether
customthe aqueous phase is separated
additionby adding concentrated HCl
customThe precipitate formed
customdried

Quellen und Nachweise

ORD-Eintrag: ord-9edd3216b4c04336a113c215dc3d42bf
Quelldatensatz: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05830906

Verknüpfte Notizen

Wird geladen…