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1-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid → HCID 86631298, Verbindung

HRID 1260925
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1260925
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([C@H:10]2[C@H:15]([N:16]([CH3:33])[C:17](=[O:32])[C:18]3[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[C:20]([C:28]([F:31])([F:30])[F:29])[CH:19]=3)[CH2:14][CH2:13][NH:12][CH2:11]2)[CH:6]=[CH:7][C:8]=1[Cl:9].[C:34]([N:41]1[CH2:49][CH2:48][CH:44]([C:45](O)=[O:46])[CH2:43][CH2:42]1)([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35]>CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.O>[F:27][C:24]([F:25])([F:26])[C:22]1[CH:23]=[C:18]([C:17]([N:16]([CH3:33])[C@@H:15]2[CH2:14][CH2:13][N:12]([C:45]([CH:44]3[CH2:48][CH2:49][N:41]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:42][CH2:43]3)=[O:46])[CH2:11][C@H:10]2[C:5]2[CH:6]=[CH:7][C:8]([Cl:9])=[C:3]([Cl:2])[CH:4]=2)=[O:32])[CH:19]=[C:20]([C:28]([F:31])([F:29])[F:30])[CH:21]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 86631295HCID 86631295, Verbindung

Produkt 1

HCID 86631298HCID 86631298, VerbindungAusbeute 99,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 757711-HydroxybenzotriazoleKatalysator
HCID 2723939
1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride
Katalysator
HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of N-[(3R*,4R*)-3-(3,4-dichlorophenyl)piperidin-4-yl]-N-methyl-3,5-bis(trifluoromethyl)benzamide monohydrochloride (0.90 g) obtained in Example 2, N-Boc-isonipecotic acid (1.52 g), WSC.HCl (0.82 mg) and HOBt (0.65 mg) was stirred at room temperature for 2 hr. The reaction mixture was poured into water, and the resultant product was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and brine and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 50→100% ethyl acetate/hexane, then 0→10% methanol/ethyl acetate) to give the title compound (1.19 g, 59%) as a white powder.

Aufarbeitung

  1. extractionthe resultant product was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (solvent gradient

Quellen und Nachweise

ORD-Eintrag
ord-21f40dc9d9474169a0f23f20fd380248
Quelldatensatz
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08470816B2

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