Hydrochloric Acid → 1,2,3,4-Tetrahydro-isoquinoline-1-carboxylic acid methyl ester hydrochloride

HRID 1921230Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1921230
C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]1[C:18]([OH:20])=[O:19])=O)(C)(C)C.[C:21](=O)([O-])[O-].[K+].[K+].IC.[ClH:29].O1CCOCC1>CN(C=O)C.C(OCC)(=O)C>[ClH:29].[CH:9]1([C:18]([O:20][CH3:21])=[O:19])[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:16][CH2:17][NH:8]1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 152807232-(tert-Butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

Produkt 1

HCID 201363151,2,3,4-Tetrahydro-isoquinoline-1-carboxylic acid methyl ester hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 2-(tert-butyoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid (0.500 g, 1.80 mmol), potassium carbonate (0.324 g, 2.34 mmol), and iodomethane (0.384 g, 2.70 mmol) in 3 mL of DMF was stirred at rt for 3 hours. The mixture was diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. To a solution of the resultant residue (0.400 g, 1.37 mmol) was added 4 N HCl in dioxane (2.06 mL, 8.22 mmol). After 2 hours, the reaction was concentrated in vacuo to provide the title compound as a beige solid that gave a mass ion (ES+) of 192.2. This crude intermediate was used to prepare Example 12, by the procedure described for Example 1.

Aufarbeitung

  1. washwashed with saturated aqueous sodium bicarbonate and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. concentrationthe reaction was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-febd630b8223496c86906d768765572e
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173672B2

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