2-Methylpyrazine → HCID 54206036, 화합물

HRID 486480

반응식

HRID 486480 반응식
[CH3:1][C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1.C([N-]C(C)C)(C)C.[Li+].[C:16]1([C:22](=[O:34])[C:23]([O:25][C@@H:26]2[CH:31]3[CH2:32][CH2:33][N:28]([CH2:29][CH2:30]3)[CH2:27]2)=[O:24])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O1CCCC1>[OH:34][C:22]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([CH2:1][C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1)[C:23]([O:25][C@@H:26]1[CH:31]2[CH2:30][CH2:29][N:28]([CH2:33][CH2:32]2)[CH2:27]1)=[O:24]

참가 물질

5

반응물 3

HCID 79762-MethylpyrazineHCID 2724682Lithium diisopropylamideHCID 228507002-oxo-2-phenylacetic acid (3R)-1-azabicyclo[2.2.2]oct-3-yl ester

생성물 1

HCID 54206036HCID 54206036, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매4회

실험 절차

2-Methylpyrazine (0.94 g) in tetrahydrofuran (THF) (5 ml) was added dropwise to lithium diisopropylamide (LDA) (7.51 ml of a 1.5 molar solution in THF) in THF (20 ml) at -78° C. After 0.75 hour a solution of (R)-3-quinuclidinyl 2-phenylglyoxalate (see Preparation 2) (2.59 g) in THF (20 ml) was added, the reaction mixture was allowed to reach room temperature, stirred for 1 hour and partitioned between ethyl acetate and 10% aqueous potassium carbonate. The organic layer was then dried over magnesium sulphate and evaporated to leave a residue which was purified by chromatography on silica gel performing a gradient elution using chloroform plus methanol (0→15%). Appropriate fractions were combined and evaporated to give the title compound, as a yellow oil (1.4 g, 39%).

후처리

  1. customto reach room temperature
  2. custompartitioned between ethyl acetate and 10% aqueous potassium carbonate
  3. dry with materialThe organic layer was then dried over magnesium sulphate
  4. customevaporated
  5. customto leave a residue which
  6. customwas purified by chromatography on silica gel performing
  7. washa gradient elution
  8. customevaporated

출처 및 근거

ORD 기록
ord-4d2a6e14c26f4d4594f72d9e9719aae0
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05292749

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