Hydrochloric Acid → (5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanol

HRID 2204558노트

반응식

HRID 2204558 반응식
[S:1]([N:11]1[C:15]2=[N:16][CH:17]=[C:18]([CH:20]=[O:21])[N:19]=[C:14]2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[BH4-].[Na+].Cl>CCO.O1CCOCC1>[S:1]([N:11]1[C:15]2=[N:16][CH:17]=[C:18]([CH2:20][OH:21])[N:19]=[C:14]2[CH:13]=[CH:12]1)([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=1)(=[O:2])=[O:3]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 580098835-tosyl-5H-pyrrolo[2,3-b]pyrazine-2-carbaldehyde

생성물 1

HCID 58010025(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanol수율 95%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 312751,4-Dioxane용매

실험 절차

To a solution of 5-tosyl-5H-pyrrolo[2,3-b]pyrazine-2-carbaldehyde (37.6 g, 125 mmol) in EtOH (500 mL) and 1,4-dioxane (500 mL) was added NaBH4 (4.72 g, 125 mmol) in one portion. After about 3 h, aqueous HCl (1N, 400 mL) was slowly added to the reaction mixture. The mixture was concentrated to one-half the original volume under reduced pressure and EtOAc (1000 mL) and water (500 mL) were added to the mixture. The layers were separated and the aqueous layer was extracted with EtOAc (500 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to provide (5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)methanol (35.9 g, 95% yield) as a tan solid: LC/MS (Table 2, Method a) Rt=1.97 min; MS m/z: 304 (M+H)+.

후처리

  1. concentrationThe mixture was concentrated to one-half the original volume under reduced pressure and EtOAc (1000 mL) and water (500 mL)
  2. additionwere added to the mixture
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAc (500 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-7251b12c97d94ff29a383b1ddcf4faeb
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365579B2

반응 노트

불러오는 중…