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

HRID 1843968ノート

反応式

HRID 1843968 の反応式
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

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 96.52%

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

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).

後処理

  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

出典と根拠

ORDレコード
ord-e993270ffbbd4f8f8c0f75807bf2bc26
出典データセット
uspto-grants-2015_02
特許番号
US08946260B2

反応ノート

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