tert-Butyl 4-(4-(((benzyloxy)carbonyl)amino)-3-ethylphenyl)-5,6-dihydropyridine-1(2H)-carboxylate → 4-(4-Amino-3-ethyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 2272428Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2272428
C(OC([NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH:19]=2)=[CH:14][C:13]=1[CH2:31][CH3:32])=O)C1C=CC=CC=1>C(O)C.[Pd]>[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]2[CH2:19][CH2:20][N:21]([C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[CH2:22][CH2:23]2)=[CH:14][C:13]=1[CH2:31][CH3:32]

Komponenten

4

Edukt 1

HCID 71232505tert-Butyl 4-(4-(((benzyloxy)carbonyl)amino)-3-ethylphenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Produkt 1

HCID 866758434-(4-Amino-3-ethyl-phenyl)-piperidine-1-carboxylic acid tert-butyl esterAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel2×

Versuchsvorschrift

tert-Butyl 4-(4-(((benzyloxy)carbonyl)amino)-3-ethylphenyl)-5,6-dihydropyridine-1(2H)-carboxylate (I39) (0.500 g, 1.14 mmol) was dissolved in ethanol (20 mL), and a slurry of 10% Pd/C (0.25 g) in ethanol (2 mL) was added. The mixture was stirred under hydrogen for 18 hours, then filtered through celite, washing the celite with ethanol (30 mL). The combined filtrates were evaporated, and chromatography (12 g silica cartridge, 0-80% ethyl acetate/petroleum benzine 40-60° C.) gave the title compound (I40) (0.212 g, 61% yield) as a pink syrup; 1H NMR (400 MHz, CDCl3) δ 6.90 (d, J=2.0 Hz, 1H), 6.87 (dd, J=8.0, 2.1 Hz, 1H), 6.63 (d, J=8.0 Hz, 1H), 4.21 (s, 2H), 3.55 (s, 2H), 2.78 (t, J=12.2 Hz, 2H), 2.59-2.46 (m, 3H), 1.78 (d, J=13.2 Hz, 2H), 1.66-1.53 (m, overlaps with water), 1.48 (s, 9H), 1.25 (t, J=7.5 Hz, 3H). LCMS Method C: rt 5.33 min; m/z 249.2 [M-tBu+2H]+, 205.2 [M-Boc+2H]+.

Aufarbeitung

  1. filtrationfiltered through celite
  2. washwashing the celite with ethanol (30 mL)
  3. customThe combined filtrates were evaporated

Quellen und Nachweise

ORD-Eintrag
ord-a3c7599c2c974a30864dca474b7e6cd7
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09120761B2

Notizen zur Reaktion

Wird geladen…