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

HRID 1921230ノート

反応式

HRID 1921230 の反応式
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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-febd630b8223496c86906d768765572e
出典データセット
uspto-grants-2012_05
特許番号
US08173672B2

反応ノート

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