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

HRID 1843968

반응식

HRID 1843968 반응식
C(O)(=O)C.[Br:5][C:6]1[CH:13]=[N:12][CH:11]=[CH:10][C:7]=1[CH:8]=O.[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.CCCCCC.C(OC(=O)C)C>[Br:5][C:6]1[CH:13]=[N:12][CH:11]=[CH:10][C:7]=1[CH2:8][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 96.52%

시약·촉매·용매 3

HCID 111,2-Dichloroethane용매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

실험 절차

Catalytic amount of acetic acid (0.3 mL) was added to a mixture of 3-bromoisonicotinaldehyde (200 mg, 1.075 mmol) and pyrrolidine (0.12 mL, 1.34 mmol) in DCE (20 mL) under nitrogen atmosphere and the resulting mixture was stirred at room temperature for 2.3 hours. This was followed by the addition of sodium triacetoxy-borohydride (342 mg, 1.612 mmol) at 0° C. The reaction mixture was stirred at room temperature overnight. The reaction was monitored by TLC (50% ethylacetate in hexane). The reaction mixture was washed with NaHCO3 solution and separated the layers. The organic layer was dried over Na2SO4 and concentrated to afford 250 mg of the product (96.52% yield).

후처리

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. washThe reaction mixture was washed with NaHCO3 solution
  3. customseparated the layers
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e993270ffbbd4f8f8c0f75807bf2bc26
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946260B2

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