Acetic Acid → 3-Bromo-4-(pyrrolidin-1-ylmethyl)pyridine

HRID 2383920

반응식

HRID 2383920 반응식
C(O)(=O)C.[Br:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][C:11]=1[CH:12]=O.[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl.CCCCCC.C(OCC)(=O)C>[Br:5][C:6]1[CH:7]=[N:8][CH:9]=[CH:10][C:11]=1[CH2:12][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 27629973-Bromopyridine-4-carboxaldehydeHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 596361363-Bromo-4-(pyrrolidin-1-ylmethyl)pyridine수율 98.2%

시약·촉매·용매 3

HCID 111,2-Dichloroethane용매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

실험 절차

Acetic acid (0.1 mL) was added to a stirred solution of 3-bromo-pyridine-4-carbaldehyde (220 mg, 1.18 mmol) and pyrrolidine (0.11 mL, 1.34 mmol) in DCE (15 mL) under nitrogen atmosphere and stirred at room temperature for 2 hours. This was followed by addition of NaBH(OAc)3 (342 mg, 1.612 mmol) at 0° C. over a period of 10 minutes. The resulting reaction mass was stirred for 12 hours at room temperature. The reaction was monitored by TLC (30% ethyl acetate in hexane). The reaction mixture was washed with NaHCO3 solution and extracted using ethyl acetate. The organic layer was dried over Na2SO4 and concentrated to afford 275 mg of the product (98.2% yield).

후처리

  1. customThe resulting reaction mass
  2. stirringwas stirred for 12 hours at room temperature
  3. washThe reaction mixture was washed with NaHCO3 solution
  4. extractionextracted
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ba2945e817e84d48a68db6216bdc198c
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263635B2

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