Potassium Carbonate → 4-[4-(3,4-Dihydro-1-methylpyrrolo[1,2-a]pyrazin-6-yl)phenoxy]butan-2-ol fumarate

HRID 486581노트

반응식

HRID 486581 반응식
[OH:1][CH:2]([CH3:16])[CH2:3][CH2:4]OS(C1C(C)=CC=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].[OH:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[N:34]3[CH2:35][CH2:36][N:37]=[C:38]([CH3:39])[C:33]3=[CH:32][CH:31]=2)=[CH:26][CH:25]=1.[OH-].[Na+].[C:42]([OH:49])(=[O:48])/[CH:43]=[CH:44]/[C:45]([OH:47])=[O:46]>CC(=O)CC.C(O)C>[C:42]([OH:49])(=[O:48])/[CH:43]=[CH:44]/[C:45]([OH:47])=[O:46].[CH3:39][C:38]1[C:33]2[N:34]([C:30]([C:27]3[CH:26]=[CH:25][C:24]([O:23][CH2:4][CH2:3][CH:2]([OH:1])[CH3:16])=[CH:29][CH:28]=3)=[CH:31][CH:32]=2)[CH2:35][CH2:36][N:37]=1

참가 물질

8

반응물 5

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 444972Fumaric AcidHCID 86747633Toluenesulphonic acid 3-hydroxybutan-1-yl esterHCID 1357369333,4-Dihydro-6-(4-hydroxyphenyl)-1-methylpyrrolo[1,2-a]pyrazine

생성물 1

HCID 190953894-[4-(3,4-Dihydro-1-methylpyrrolo[1,2-a]pyrazin-6-yl)phenoxy]butan-2-ol fumarate수율 90%

시약·촉매·용매 2

HCID 702Ethanol용매2회HCID 6569Methyl Ethyl Ketone용매

실험 절차

Toluenesulphonic acid 3-hydroxybutan-1-yl ester (1.8 g) and 1.8 g of potassium carbonate was added at room temperature while stirring and under argon to a solution of 1.5 g of 3,4-dihydro-6-(4-hydroxyphenyl)-1-methylpyrrolo[1,2-a]pyrazine in 20 ml of 2-butanone and the mixture was boiled for 20 hours. The cooled reaction mixture was treated with 100 ml of 2N sodium hydroxide solution and extracted three times with 200 ml of methylene chloride each time. The organic phases were washed twice with 100 ml of water each time, combined, dried with MgSO4 and freed from solvent. The residue, 2.4 g of brown oil, was chromatographed on 50 g of silica gel with methylene chloride/methanol mixtures (50:1 to 20:1) as the eluent. There were obtained 1.2 g of an orange coloured, amorphous solid which was dissolved in a 25-fold amount of ethanol and treated while hot with 1.1 equivalents of a saturated solution of fumaric acid in ethanol. There were obtained 1.5 g (90%) of 4-[4-(3,4-dihydro-1-methylpyrrolo[1,2-a]pyrazin-6-yl)phenoxy]butan-2-ol fumarate (1:1); m.pt.: 156°-157° C. (dec.).

후처리

  1. customThe cooled reaction mixture
  2. extractionextracted three times with 200 ml of methylene chloride each time
  3. washThe organic phases were washed twice with 100 ml of water each time
  4. dry with materialdried with MgSO4
  5. customThe residue, 2.4 g of brown oil, was chromatographed on 50 g of silica gel with methylene chloride/methanol
  6. customThere were obtained 1.2 g of an orange coloured, amorphous solid which

출처 및 근거

ORD 기록
ord-352821f482ef425f8db03bdfcb9ee2e1
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05292732

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