Acetonitrile → HCID 86680289, Verbindung

HRID 2202597

Reaktionsgleichung

Reaktionsgleichung von HRID 2202597
[CH:1]([O:14][C@@H:15]1[CH2:19][CH2:18][NH:17][CH2:16]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:21][C:22]1[N:27]=[C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:25]=[CH:24][CH:23]=1.C(#N)C.C(N(CC)CC)C>C(OCC)(=O)C>[CH:1]([O:14][C@@H:15]1[CH2:19][CH2:18][N:17]([CH2:21][C:22]2[N:27]=[C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:25]=[CH:24][CH:23]=2)[CH2:16]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 15614003Ethyl 6-(chloromethyl)pyridine-2-carboxylateHCID 70647884(R)-3-benzhydryloxypyrrolidine

Produkt 1

HCID 86680289HCID 86680289, VerbindungAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 8.144 g of (R)-3-benzhydryloxypyrrolidine synthesized in Production Example 168, 7.701 g of a known compound ethyl 6-chloromethylpyridine-2-carboxylate, 69 mL of acetonitrile, and 9.0 mL of triethylamine was heated under reflux for 3 hours. After being allowed to cool down, the mixture was diluted with ethyl acetate. The diluted mixture was poured into a saturated saline solution, and the organic layer was collected by separation. The organic layer was washed with a saturated saline solution and dried over magnesium sulfate. The solvent was distilled off, and then the residue was purified by silica gel column chromatography (chloroform/acetone (volume ratio)=15:1 to 10:1) to give the title compound (7.22 g (54%)).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. temperatureto cool down
  4. additionThe diluted mixture was poured into a saturated saline solution
  5. customthe organic layer was collected by separation
  6. washThe organic layer was washed with a saturated saline solution
  7. dry with materialdried over magnesium sulfate
  8. distillationThe solvent was distilled off
  9. customthe residue was purified by silica gel column chromatography (chloroform/acetone (volume ratio)=15:1 to 10:1)

Quellen und Nachweise

ORD-Eintrag
ord-87ead9f29d3c44d09a18ab4650c96571
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365553B2

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