1-Methyl-4-piperidone → 1-Methyl-4-(5-(2-methyl-1,3-dioxolan-2-yl)pyridin-2-yl)piperidin-4-ol

HRID 1853481

반응식

HRID 1853481 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:13])[O:12][CH2:11][CH2:10][O:9]2)=[CH:4][N:3]=1.[Li]CCCC.[CH3:19][N:20]1[CH2:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]1>O1CCCC1>[CH3:19][N:20]1[CH2:25][CH2:24][C:23]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3([CH3:13])[O:12][CH2:11][CH2:10][O:9]3)=[CH:4][N:3]=2)([OH:26])[CH2:22][CH2:21]1

참가 물질

5

반응물 3

HCID 740491-Methyl-4-piperidoneHCID 857750992-Bromo-5-(2-methyl-1,3-dioxolan-2-yl)pyridineHCID 178418339Butyllithium

생성물 1

HCID 574658461-Methyl-4-(5-(2-methyl-1,3-dioxolan-2-yl)pyridin-2-yl)piperidin-4-ol수율 85%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

2-bromo-5-(2-methyl-1,3-dioxolan-2-yl)pyridine (500 mg, 2.048 mmol) (described in the literature: Bioorg. Med. Chem., 2005, 13, 6763) was dissolved in anhydrous tetrahydrofuran (10 mL) and cooled to −78° C. under nitrogen. n-BuLi (901.2 μL of 2.5 M, 2.253 mmol) was added dropwise and the reaction mixture was stirred at −78° C. for 30 minutes. 1-Methyl-4-piperidone (602.6 mg, 655.0 μL, 5.325 mmol) was added and the reaction was allowed to stir at −78° C. for 20 minutes then warmed slowly to ambient temperature. The reaction mixture was stirred at room temperature for 18 hours and concentrated in vacuo. The residue was purified on silica gel by flash column chromatography to afford the title compound as a sticky orange solid (483.4 mg, 85% yield).

후처리

  1. stirringto stir at −78° C. for 20 minutes
  2. temperaturethen warmed slowly to ambient temperature
  3. stirringThe reaction mixture was stirred at room temperature for 18 hours
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified on silica gel by flash column chromatography

출처 및 근거

ORD 기록
ord-3a09eb135c464493bad342fe7685d6d6
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962642B2

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