Hydrochloric Acid → (R)-1-[3-(2-Pyrrolidinyl)-2-propynyl] pyrrolidine, dihydrochloride

HRID 359472노트

반응식

HRID 359472 반응식
[N:1]1([CH2:6][C:7]#[C:8][C@H:9]2[CH2:13][CH2:12][CH2:11][N:10]2C(OC(C)(C)C)=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)C.[ClH:24]>CO>[ClH:24].[ClH:24].[NH:10]1[CH2:11][CH2:12][CH2:13][C@@H:9]1[C:8]#[C:7][CH2:6][N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 9860463(R)-t-butyl 2-[3-(1-pyrrolidinyl)-1-propynyl]-1-pyrrolidinecarboxylate

생성물 1

HCID 14730293(R)-1-[3-(2-Pyrrolidinyl)-2-propynyl] pyrrolidine, dihydrochloride

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
80 °C

실험 절차

A mixture of 7.0 g of (R)-2-[3-(1- pyrrolidinyl)-1-propynyl]-1-pyrrolidinecarboxylic acid, 1,1-dimethylethyl ester, 61 ml of ethanol and 61 ml of 2N hydrochloric acid is heated at 80° C. for one hour. The reaction is concentrated in vacuo and the residue is extracted with methylene chloride. The aqueous layer is concentrated in vacuo, made basic with 10N sodium hydroxide and extracted with methylene chloride. The methylene chloride solution is dried over sodium sulfate, filtered and concentrated in vacuo. The residue is dissolved in methanol, treated with an excess of methanolic hydrogen chloride and precipitated with the addition of diethyl ether. The dihydrochloride is recrystallized from hot methanol to give pure product, mp 198°-200° C. with decomposition, [α]D26° =+21°±1 (C=1.012%, methanol).

후처리

  1. concentrationThe reaction is concentrated in vacuo
  2. extractionthe residue is extracted with methylene chloride
  3. concentrationThe aqueous layer is concentrated in vacuo
  4. extractionextracted with methylene chloride
  5. dry with materialThe methylene chloride solution is dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. dissolutionThe residue is dissolved in methanol
  9. additiontreated with an excess of methanolic hydrogen chloride
  10. customprecipitated with the addition of diethyl ether
  11. customThe dihydrochloride is recrystallized from hot methanol
  12. customto give pure product, mp 198°-200° C. with decomposition, [α]D26° =+21°

출처 및 근거

ORD 기록
ord-1212f309045b4a95affb6168ede9a450
출처 데이터셋
uspto-grants-1991_03
특허 번호
US05001142

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