Carbon Dioxide → 4-(3-Fluoropyrazin-2-YL)tetrahydro-2H-pyran-4-OL

HRID 555853노트

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HRID 555853 반응식
CC1(C)CCCC(C)(C)N1.C(=O)=O.[F:14][C:15]1[CH:20]=[N:19][CH:18]=[CH:17][N:16]=1.[O:21]1[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]1>C1COCC1.CCCCCC>[F:14][C:15]1[C:20]([C:24]2([OH:27])[CH2:25][CH2:26][O:21][CH2:22][CH2:23]2)=[N:19][CH:18]=[CH:17][N:16]=1

참가 물질

7

반응물 4

HCID 280Carbon Dioxide2회HCID 130352,2,6,6-TetramethylpiperidineHCID 121599Tetrahydro-4H-pyran-4-oneHCID 6428352-Fluoropyrazine

생성물 1

HCID 593512304-(3-Fluoropyrazin-2-YL)tetrahydro-2H-pyran-4-OL

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

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온도
0 °C

실험 절차

A 2.5M solution of nbuli (4.49 mL, 11.22 mmol)/hexane in THF (3 mL) was first cooled to −78° C. To the cooled solution was added dropwise, 2,2,6,6-tetramethylpiperidine (2.065 mL, 12.24 mmol). The dry ice bath was then switched to a 0° C. bath. The reaction mixture was stirred for 10 min at 0° C. and then the dry ice bath was switched back to recool the reaction mixture to −78° C. To the cooled solution was added 2-fluoropyrazine (1 g, 10.20 mmol), dropwise. After 5 min of stirring at −78° C., a solution of dihydro-2H-pyran-4(3H)-one (0.937 mL, 10.20 mmol) in 0.6 mL of THF was added dropwise. The resulting mixture was allowed to gradually warm to room temperature overnight. Reaction was quenched with saturated NH4Cl and extracted with EtOAc. Purification by Biotage (0-100% EtOAc/hexane) produced product.

후처리

  1. additionTo the cooled solution was added dropwise
  2. customwas then switched to a 0° C.
  3. customto −78° C
  4. stirringAfter 5 min of stirring at −78° C.
  5. temperatureto gradually warm to room temperature overnight
  6. customReaction
  7. customwas quenched with saturated NH4Cl
  8. extractionextracted with EtOAc
  9. customPurification by Biotage (0-100% EtOAc/hexane)
  10. customproduced product

출처 및 근거

ORD 기록
ord-159c35b1176f47b795e16e9f409273dc
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08053438B2

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