Dichloromethane → 1-Acetyl-3-Aminopyrrolidine

HRID 1373687노트

반응식

HRID 1373687 반응식
[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]

참가 물질

6

반응물 4

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

생성물 2

HCID 112172651-Acetyl-3-AminopyrrolidineHCID 23079655HCID 23079655, 화합물

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f242749d01864d4b81167f54ba3a3a81
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07163928B2

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