1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-Benzyl-6-[(3R,4R)-3,4-dihydroxypyrrolidin-1-yl]pyridine

HRID 2216340노트

반응식

HRID 2216340 반응식
FC(F)(F)S(O[C:7]1[N:12]=[C:11]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:10]=[CH:9][CH:8]=1)(=O)=O.C(O)(=O)C.[OH:26][C@H:27]1[C@H:31]([OH:32])[CH2:30][NH:29][CH2:28]1.C(O)(=O)[C@H]([C@@H](C(O)=O)O)O.C1CCN2C(=NCCC2)CC1>CN1CCCC1=O>[CH2:13]([C:11]1[CH:10]=[CH:9][CH:8]=[C:7]([N:29]2[CH2:30][C@@H:31]([OH:32])[C@H:27]([OH:26])[CH2:28]2)[N:12]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

참가 물질

6

반응물 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 439655D-Tartaric acidHCID 219422892-Benzyl-6-pyridyl trifluoromethanesulfonateHCID 69363142(3R,4R)-3,4-dihydroxypyrrolidine acetate

생성물 1

HCID 693610072-Benzyl-6-[(3R,4R)-3,4-dihydroxypyrrolidin-1-yl]pyridine수율 55.6%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

To a mixture of 11.3 g of 2-benzyl-6-pyridyl trifluoromethanesulfonate, 11.3 g of (3R,4R)-3,4-dihydroxypyrrolidine acetate (synthesized from D-tartaric acid as a starting material, Angew. Chem. Int. Ed. Engl., 23(6), 435, 1984) and 10 ml of N-methylpyrrolidone was added dropwise 11 ml of 1,8-diazabicyclo[5.4.0]-7-undecene under nitrogen atmosphere in an oil bath at 100° C., followed by heating under stirring for 6 hours. After standing to cool, the reaction mixture was extracted with ethyl acetate-water. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (ethyl acetate), to give 5.35 g of the title compound.

후처리

  1. temperatureby heating
  2. temperatureto cool
  3. extractionthe reaction mixture was extracted with ethyl acetate-water
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate)

출처 및 근거

ORD 기록
ord-10f82bad50794a4bae4cebeca9eeec32
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07112593B2

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