Trifluoroacetic acid → Methyl 1-benzylpyrrolidine-3-carboxylate

HRID 129826

반응식

HRID 129826 반응식
[C:1]([O:5][CH2:6]C)(=[O:4])[CH:2]=[CH2:3].[CH2:8]([N:15]([CH2:21]OC)[CH2:16][Si](C)(C)C)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.FC(F)(F)C(O)=O>ClCCl>[CH2:8]([N:15]1[CH2:21][CH2:3][CH:2]([C:1]([O:5][CH3:6])=[O:4])[CH2:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 8821Ethyl AcrylateHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine

생성물 1

HCID 4610751Methyl 1-benzylpyrrolidine-3-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Ethyl acrylate (86 g, 1.0 mole) in dichloromethane (2 L) was cooled to 0° C. and treated with N-benzyl-N-(methoxymethyl)-N-[(trimethylsilyl)methyl]amine (compound D17 of EP 0363085) (300 g, 80% pure by 1H NMR, 1 mole) with stirring over a period of 10 min whilst maintaining the temperature between -5° C. and 0° C. A solution of trifluoroacetic acid in dichloromethane (100 ml, 1 molar) was added at such a rate that the temperature did not rise above 5° C. and the reaction allowed to warm to room temperature overnight. The solution was then washed with saturated aqueous potassium carbonate solution, dried over sodium sulphate and concentrated in vacuo to a gum. The glum was distilled in vacuo to afford the title compound. (D4) as a single main fraction. Bpt 150°-160° at 8 mm (232 g, 100%).

후처리

  1. temperaturewhilst maintaining the temperature between -5° C. and 0° C
  2. customdid not rise above 5° C.
  3. washThe solution was then washed with saturated aqueous potassium carbonate solution
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo to a gum
  6. distillationThe glum was distilled in vacuo

출처 및 근거

ORD 기록
ord-c7013366f2ce4f4ea80eb3c86ea0cf70
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05470859

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