Methanol → 7-Hydroxymethyl-8-methoxy-2-(2-trimethylsilanyl-ethoxymethyl)-2H-[1,2,4]triazolo[4,3-a]pyridin-3-one

HRID 1037310노트

반응식

HRID 1037310 반응식
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]2[C:11](=[O:22])[N:12]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[N:13]=[C:7]2[C:6]=1[O:23][CH3:24])=O.CC(C[AlH]CC(C)C)C.CO.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C(Cl)Cl>[OH:2][CH2:3][C:5]1[CH:10]=[CH:9][N:8]2[C:11](=[O:22])[N:12]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:19])([CH3:21])[CH3:20])[N:13]=[C:7]2[C:6]=1[O:23][CH3:24]

참가 물질

6

반응물 4

HCID 887MethanolHCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydrideHCID 670678768-Methoxy-3-oxo-2-(2-trimethylsilanyl-ethoxymethyl)-2,3-dihydro-[1,2,4]triazolo[4,3-a]pyridine-7-carboxylic acid methyl ester

생성물 1

HCID 670678957-Hydroxymethyl-8-methoxy-2-(2-trimethylsilanyl-ethoxymethyl)-2H-[1,2,4]triazolo[4,3-a]pyridin-3-one수율 89%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

반응 조건

온도
-50 °C

실험 절차

To a stirred solution of 8-methoxy-3-oxo-2-(2-trimethylsilanyl-ethoxymethyl)-2,3-dihydro-[1,2,4]triazolo[4,3-a]pyridine-7-carboxylic acid methyl ester (1.51 g, 4.27 mmol) in dry DCM (50 mL), cooled to −78° C., was added 1 M DIBAL in DCM (8.54 mL, 8.54 mmol) over 3 minutes. The reaction mixture was allowed to warm to −50° C. over 45 minutes, followed by cooling to −78° C. and addition of MeOH (5 mL) to quench the reaction. The reaction mixture was allowed to warm to 0° C. and was diluted with DCM. An aqueous solution of Rochelle salt (200 mL, 10% w/v) was added and the mixture was stirred vigorously for 30 minutes. The aqueous phase was isolated and extracted with DCM. The combined organic phases were washed with water, dried (Na2SO4), filtered, and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 50 to 100% EtOAc in cyclohexane) to afford the title compound (1.23 g, 89%) as a pale yellow solid. LCMS (Method A): RT=4.18 min, [M+H]+=326.

후처리

  1. temperatureby cooling to −78° C.
  2. customto quench
  3. customthe reaction
  4. temperatureto warm to 0° C.
  5. customThe aqueous phase was isolated
  6. extractionextracted with DCM
  7. washThe combined organic phases were washed with water
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-72c8fa9b01794e89a112d3fe0000d5de
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546376B2

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