Dichloromethane → 1-Acetyl-3-Aminopyrrolidine

HRID 1373687ノート

反応式

HRID 1373687 の反応式
[CH3:1][O:2]C1C=C(C=CC=1OC)C=[N:7][CH:8]1[CH2:12][CH2:11][NH:10][CH2:9]1.C(N(CC)CC)C.[C:25]([Cl:28])(=[O:27])[CH3:26].[CH2:29]([Cl:31])[Cl:30]>>[CH:29]([Cl:28])([Cl:31])[Cl:30].[CH3:1][OH:2].[NH3:7].[CH3:25][OH:27].[C:25]([N:10]1[CH2:11][CH2:12][CH:8]([NH2:7])[CH2:9]1)(=[O:27])[CH3:26]

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 21074591(3,4-Dimethoxy-benzylidene)-pyrrolidin-3-yl-amine

生成物 2

HCID 112172651-Acetyl-3-AminopyrrolidineHCID 23079655HCID 23079655、化合物

実験手順

To (3,4-dimethoxy-benzylidene)-pyrrolidin-3-yl-amine (3 mmol) in dry methylene chloride (30 mL) and triethylamine (7.5 mmol) at room temperature was added acetyl chloride (3.5 mmol) dropwise. The mixture was stirred for 6 hours at room temperature, then the solvent removed under reduced pressure. The residue was dissolved in a mixture of methanesulfonic acid (3.84 g) in 20 mL tetrahydrofuran:water (3:1) and stirred for 60 hours. The solution was neutralized with solid sodium carbonate, filtered, and solvent removed from the filtrate under reduced pressure. The residue was purified by silica gel flash chromatography column, eluting firstly with CHCl3—cC6H12—MeOH (85-14-1, 1.0 1) to elute the faster moving spots, and then with CHCl3—MeOH—NH3/MeOH (93-5-2), to obtain 1-acetyl-3-aminopyrrolidine, a compound of formula (4) as an oil.

後処理

  1. customthe solvent removed under reduced pressure
  2. dissolutionThe residue was dissolved in a mixture of methanesulfonic acid (3.84 g) in 20 mL tetrahydrofuran:water (3:1)
  3. stirringstirred for 60 hours
  4. filtrationfiltered
  5. customsolvent removed from the filtrate under reduced pressure
  6. customThe residue was purified by silica gel flash chromatography column
  7. washeluting firstly with CHCl3—cC6H12—MeOH (85-14-1, 1.0 1)
  8. washto elute the

出典と根拠

ORDレコード
ord-f242749d01864d4b81167f54ba3a3a81
出典データセット
uspto-grants-2007_01
特許番号
US07163928B2

反応ノート

読み込み中…