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Triethylamine → cis-2-Hydroxy-1-{4-[4-(octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-piperidin-1-yl}-ethanone

HRID 1809069
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1809069
[N:1]1([C:11]([C:13]2[CH:17]=[C:16]([CH:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[S:15][CH:14]=2)=[O:12])[C@@H:10]2[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.C(O)(=O)C.[C:35](Cl)(=[O:38])[CH2:36][OH:37].C[O-].[Na+]>C(Cl)Cl.CO>[OH:38][CH2:35][C:36]([N:21]1[CH2:20][CH2:19][CH:18]([C:16]2[S:15][CH:14]=[C:13]([C:11]([N:1]3[C@@H:10]4[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]4)[CH2:4][CH2:3][CH2:2]3)=[O:12])[CH:17]=2)[CH2:23][CH2:22]1)=[O:37]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 10942334Sodium MethoxideHCID 86646702cis-(Octahydro-quinolin-1-yl)-(5-piperidin-4-yl-thiophen-3-yl)-methanoneHCID 131730178Glycolic acid chloride acetate

Produkt 1

HCID 86646704cis-2-Hydroxy-1-{4-[4-(octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-piperidin-1-yl}-ethanoneAusbeute 25,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of cis-(octahydro-quinolin-1-yl)-(5-piperidin-4-yl-thiophen-3-yl)-methanone (CC-033) (0.061 g, 0.18 mmol) in DCM (1 mL) was added triethylamine (0.55 mmol) and glycolic acid chloride acetate (0.24 mmol). The reaction mixture was stirred for 1 hour, and then the solvent evaporated. Methanol (1 mL) and sodium methoxide (0.91 mmol) were added and the reaction mixture was stirred overnight. The solvent was removed by evaporation and the product was purified by HPLC, eluting with 10%-98% acetonitrile in water (0.1% formic acid). The fractions containing the desired product were concentrated under vacuum to give the title compound as a colourless oil (0.018 g). LCMS m/z 391.11 [M+H]+ RT=9.24 min (Analytical Method 2).

Aufarbeitung

  1. customthe solvent evaporated
  2. stirringthe reaction mixture was stirred overnight
  3. customThe solvent was removed by evaporation
  4. customthe product was purified by HPLC
  5. washeluting with 10%-98% acetonitrile in water (0.1% formic acid)
  6. additionThe fractions containing the desired product
  7. concentrationwere concentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-bbca1605cde14904990e9517abce5929
Quelldatensatz
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08362008B2

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