Sulfuric Acid → N-(1-benzyl-3-methylpyrrolidin-3-yl)acetamide

HRID 252096

反応式

HRID 252096 の反応式
S(=O)(=O)(O)O.[CH2:6]([N:13]1[CH2:17][CH2:16][C:15]([CH3:19])(O)[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)([O-])[O-:21].[K+].[K+].[C:26](#[N:28])[CH3:27]>>[CH2:6]([N:13]1[CH2:17][CH2:16][C:15]([NH:28][C:26](=[O:21])[CH3:27])([CH3:19])[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

参加物

5

反応物 4

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 186296481-Benzyl-3-methylpyrrolidin-3-OL

生成物 1

HCID 13787481N-(1-benzyl-3-methylpyrrolidin-3-yl)acetamide

実験手順

Add concentrated sulphuric acid (16 mL) dropwise to 1-benzyl-3-methyl-pyrrolidin-3-ol (4.4 g, 23 mmol) in acetonitrile (12 mL) at 0° C. Stir and allow the resulting solution to warm up gradually to room temperature overnight. Pour onto crushed ice and add saturated aqueous potassium carbonate and extract with dichloromethane. Combine the organic layers and wash with saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate to give N-(1-benzyl-3-methylpyrrolidin-3-yl)-acetamide which may be used in the next step without further purification (4.89 g, 70%). 1H NMR (400 MHz, CDCl3) δ 7.22-7.34 (5H, m), 5.62 (1H, s), 3.57-3.66 (2H, m), 2.76-2.84 (2H, m), 2.54 (1H, td, J=8.80, 5.87 Hz), 2.47 (1H, d, J=9.78 Hz), 2.13 (1H, m), 1.90-1.93 (3H, m), 1.84-1.90 (1H, m), 1.49 (3H, s), MS (ES): m/z=233 [M+H].

後処理

  1. additionPour
  2. customonto crushed ice
  3. extractionextract with dichloromethane
  4. washwash with saturated aqueous sodium chloride
  5. dry with materialdry (magnesium sulfate)
  6. concentrationconcentrate

出典と根拠

ORDレコード
ord-84ce6ce6bac146bb9fcaaa2cd5080ec9
出典データセット
uspto-grants-2011_01
特許番号
US07868014B2

関連ノート

読み込み中…