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

HRID 2383920ノート

反応式

HRID 2383920 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 111,2-Dichloroethane溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ba2945e817e84d48a68db6216bdc198c
出典データセット
uspto-grants-2012_09
特許番号
US08263635B2

反応ノート

読み込み中…