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

HRID 1921230노트

반응식

HRID 1921230 반응식
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

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-febd630b8223496c86906d768765572e
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173672B2

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