HCID 46941716, Verbindung → Thieno[3,2-c]pyridine-2-carboxylic acid, 4,5,6,7-tetrahydro-3-methyl-, ethyl ester

HRID 468667Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 468667
[CH3:1][C:2]1[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[S:4][C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12]>C(O)C.O=[Pt]=O>[CH3:1][C:2]1[C:6]2[CH2:7][NH:8][CH2:9][CH2:10][C:5]=2[S:4][C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Komponenten

4

Edukt 1

HCID 46941716HCID 46941716, Verbindung

Produkt 1

HCID 58157568Thieno[3,2-c]pyridine-2-carboxylic acid, 4,5,6,7-tetrahydro-3-methyl-, ethyl esterAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 345198Adams' catalystKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of ethyl 3-methylthieno[3,2-c]pyridine-2-carboxylate (4 g, 0.018 mol) and PtO2 (0.5 g, 0.002 mol) in ethanol (100 mL) was stirred under an H2 atmosphere (3 atmospheres) for 72 hours at room temperature. The PtO2 was removed by filtration, the filtrate was concentrated under reduced pressure and the residue obtained was purified by silica gel chromatography (DCM/EtOH=10:1) to afford ethyl 3-methyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylate (1.6 g, 40%). ES+ 226; 1H NMR (400 MHz, DMSO) δ 4.24 (q, J=7.1 Hz, 2H), 3.93 (s, 2H), 3.21 (t, J=5.9 Hz, 2H), 2.89 (t, J=5.7 Hz, 2H), 2.55 (s, 1H), 2.34 (s, 3H), 1.26 (t, J=6.0 Hz, 3H).

Aufarbeitung

  1. customThe PtO2 was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe residue obtained
  4. customwas purified by silica gel chromatography (DCM/EtOH=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-e2ee240d61d24c0a9609394ce36b6225
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08624040B2

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