Chloroform → cis-(+-)-N-(2-(2,6-Dimethyl-1-piperidinyl)ethyl)-2-oxo-3-hydroxy-1-pyrrolidineacetamide

HRID 1087082

반응식

HRID 1087082 반응식
[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]([OH:10])=O)[C:3]1=[O:11].O[N:13]1C(=O)CC[C:14]1=O.C1(N=[C:27]=[N:28][CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)CCCCC1.[CH:35](Cl)(Cl)Cl>CN(C)C=O>[CH3:30][C@H:31]1[CH2:32][CH2:33][CH2:34][C@@H:29]([CH3:35])[N:28]1[CH2:27][CH2:14][NH:13][C:8](=[O:10])[CH2:7][N:4]1[CH2:5][CH2:6][CH:2]([OH:1])[C:3]1=[O:11]

참가 물질

6

반응물 4

HCID 6212Chloroform2회HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 19817647HCID 19817647, 화합물

생성물 1

HCID 3069833cis-(+-)-N-(2-(2,6-Dimethyl-1-piperidinyl)ethyl)-2-oxo-3-hydroxy-1-pyrrolidineacetamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

1.50 g of (R/S)-2-(3-hydroxy-2-oxo-1-pyrrolidinyl)acetic acid are dissolved in 50 ml of chloroform and 10 ml of dimethylformamide. 1.08 g of N-hydroxysuccinimide are added thereto. Thereafter, 2.08 g of dicyclohexylcarbodiimide dissolved in 25 ml of chloroform are added. The mixture is stirred at room temperature for 4 hours and then precipitated solid is filtered. The filtrate is concentrated to a volume of about 20 ml and the again filtered. The filtrate is evaporated and the residue is treated with 1.70 g of 94.7% cis-2-(2,6-dimethyl-1-piperidinyl)ethylamine. The mixture is left to stand at room temperature overnight and the excess cis-2-(2,6-dimethyl-1-piperidinyl)ethylamine is removed in vacuo. The residue is chromatographed on 60 g of aluminum oxide (activity grade I, basic). The fractions which are eluted with chloroform and alcohol are evaporated. The residue is stirred at room temperature in 35 ml of diethyl ether/ethyl acetate (2:1). There is obtained (R/S)-cis-N-[2-(2,6-dimethyl-1-piperidinyl)ethyl]- 2-(3-hydroxy-2-oxo-1-pyrrolidinyl)acetamide (melting point 116°-120°) which melts at 126°-128° after repeated chromatography on aluminum oxide (activity grade III, neutral) and recrystallization from ethyl acetate.

후처리

  1. additionare added
  2. customprecipitated solid
  3. filtrationis filtered
  4. concentrationThe filtrate is concentrated to a volume of about 20 ml
  5. filtrationthe again filtered
  6. customThe filtrate is evaporated
  7. additionthe residue is treated with 1.70 g of 94.7% cis-2-(2,6-dimethyl-1-piperidinyl)ethylamine
  8. waitThe mixture is left
  9. waitto stand at room temperature overnight
  10. customthe excess cis-2-(2,6-dimethyl-1-piperidinyl)ethylamine is removed in vacuo
  11. customThe residue is chromatographed on 60 g of aluminum oxide (activity grade I, basic)
  12. washThe fractions which are eluted with chloroform and alcohol
  13. customare evaporated
  14. stirringThe residue is stirred at room temperature in 35 ml of diethyl ether/ethyl acetate (2:1)

출처 및 근거

ORD 기록
ord-a3ff9ec47d9c43d38d11ae109afab02e
출처 데이터셋
uspto-grants-1991_07
특허 번호
US05034402

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