1,2-Dichloroethane → 1-Tert-butyl 3-ethyl 3-{2-[(4-methylpyridin-3-yl)amino]ethyl}piperidine-1,3-dicarboxylate

HRID 1044369Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1044369
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[NH2:8].O=[CH:10][CH2:11][C:12]1([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13]1.ClCCCl.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O>[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[NH:8][CH2:10][CH2:11][C:12]1([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[O:19])[CH2:13]1

Komponenten

6

Edukt 4

HCID 111,2-DichloroethaneHCID 1379353-Amino-4-picolineHCID 5049666Sodium triacetoxyborohydrideHCID 579708781-Tert-butyl 3-ethyl 3-(2-oxoethyl)piperidine-1,3-dicarboxylate

Produkt 1

HCID 667226241-Tert-butyl 3-ethyl 3-{2-[(4-methylpyridin-3-yl)amino]ethyl}piperidine-1,3-dicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

4-Methylpyridin-3-amine (36.0 mg, 0.000333 mol) was added to a solution of 1-tert-butyl 3-ethyl 3-(2-oxoethyl)piperidine-1,3-dicarboxylate (0.095 g, 0.00032 mol) in 1,2-dichloroethane (1.9 mL, 0.025 mol) and followed by sodium triacetoxyborohydride (0.20 g, 0.00095 mol) and the mixture was stirred for 24 h. The mixture was poured into pre-cooled water, extracted with ethyl acetate. The organic layer was separated, dried and concentrated. The product was purified by CombiFlash using CH2Cl2/EtOAc (max EtOAc 50%). LC-MS: 392.3 (M+H)+.

Aufarbeitung

  1. additionThe mixture was poured
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. customdried
  5. concentrationconcentrated
  6. customThe product was purified by CombiFlash

Quellen und Nachweise

ORD-Eintrag
ord-b26ab11a5bea4b4abc0c36790d1712f9
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563570B2

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