Pyrrolidine → 3-Bromo-5-(pyrrolidin-1-ylmethyl)pyridine

HRID 546643노트

반응식

HRID 546643 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=O)[CH:5]=[N:6][CH:7]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1>ClCCCl>[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([CH2:8][N:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)[CH:3]=1

참가 물질

5

반응물 3

HCID 31268PyrrolidineHCID 27847345-Bromo-3-pyridinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 212559453-Bromo-5-(pyrrolidin-1-ylmethyl)pyridine

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

To a solution of 5-bromo-3-pyridinecarboxaldehyde in 20 mL of 1,2-dichloroethane are successively added, under argon, 4.55 g of sodium triacetoxyborohydride and 0.94 mL of pyrrolidine. The reaction mixture is stirred at room temperature for 3 hours and then washed with saturated sodium hydrogen carbonate solution, with water and with saturated sodium chloride solution, dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue is purified by chromatography on a column of silica, eluting with a mixture of ethyl acetate and cyclohexane (80/20 by volume) to give 1.4 g of 3-Bromo-5-pyrrolidin-1-ylmethylpyridine in the form of a pale yellow oil.

후처리

  1. washwashed with saturated sodium hydrogen carbonate solution, with water and with saturated sodium chloride solution
  2. dry with materialdried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by chromatography on a column of silica
  6. washeluting with a mixture of ethyl acetate and cyclohexane (80/20 by volume)

출처 및 근거

ORD 기록
ord-57125a8d6a064790a21575419153c8d7
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935819B2

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