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

HRID 1921230Notes

Reaction equation

HRID 1921230 reaction equation
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

Participants

8

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-febd630b8223496c86906d768765572e
Source dataset
uspto-grants-2012_05
Patent number
US08173672B2

Reaction notes

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