(R)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine → 1,4-Bis((2R,5S)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-pyrazinyl)-but-2-yne

HRID 976016

반응식

HRID 976016 반응식
[CH3:1][O:2][C:3]1[C@@H:4]([CH:11]([CH3:13])[CH3:12])[N:5]=[C:6]([O:9][CH3:10])[CH2:7][N:8]=1.[Li][CH2:15][CH2:16][CH2:17][CH3:18].[CH3:19][O:20][C:21]1[CH:22]([CH:29]([CH3:31])[CH3:30])[N:23]=[C:24]([O:27][CH3:28])[CH2:25][N:26]=1>C1COCC1>[CH3:1][O:2][C:3]1[C@@H:4]([CH:11]([CH3:13])[CH3:12])[N:5]=[C:6]([O:9][CH3:10])[C@H:7]([CH2:18][C:17]#[C:16][CH2:15][C@H:25]2[C:24]([O:27][CH3:28])=[N:23][C@H:22]([CH:29]([CH3:31])[CH3:30])[C:21]([O:20][CH3:19])=[N:26]2)[N:8]=1

참가 물질

5

반응물 3

HCID 736066(R)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazineHCID 38009092,5-Dihydro-2-isopropyl-3,6-dimethoxypyrazineHCID 178418339Butyllithium

생성물 1

HCID 114528411,4-Bis((2R,5S)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-pyrazinyl)-but-2-yne수율 77%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

(2R)-(-)-2,5-Dihydro-3,6-dimethoxy-2-isopropylpyrazine 2.76 g (15mmol) was dissolved in 100 ml dry THF and cooled to -78° C., then 9.5 ml of a 1.6M solution BuLi (15 mmol) was added dropwise with stirring. After 1 hour 0.92 g (7.5 mmol) of 1,4-dichloro-2,3-butyne was introduced slowly. TLC and gas chromatography (GC) of the reaction mixture 1 hour later showed substantial amounts of unreacted 2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine and the monoalkylated product. The reaction was allowed to continue overnight and reach ambient temperature gradually. THF was evaporated off under reduced pressure and the residue partitioned between ether and water. The water phase was extracted twice with ether, dried (MgSO4) and evaporated. Kugelrohr distillation of the reaction mixture to give 2.3g (77%) pure product.

후처리

  1. customreach ambient temperature
  2. customTHF was evaporated off under reduced pressure
  3. customthe residue partitioned between ether and water
  4. extractionThe water phase was extracted twice with ether
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. distillationKugelrohr distillation of the reaction mixture

출처 및 근거

ORD 기록
ord-06cb4186efa54d49b3169c4ce264d158
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05610141

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