Hydrochloric Acid → (3R)-1-benzylpyrrolidin-3-amine

HRID 232050

반응식

HRID 232050 반응식
[C:1]1([CH2:7][N:8]2[CH2:12][CH2:11][C@@H:10]([N:13]3C(=O)C4C(=CC=CC=4)C3=O)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.NN.Cl>CO>[C:1]1([CH2:7][N:8]2[CH2:12][CH2:11][C@@H:10]([NH2:13])[CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 14555490[R]-2-[1-(Phenylmethyl)-3-pyrrolidinyl]-1H-isoindole-1,3(2H)-dione

생성물 1

HCID 1519354(3R)-1-benzylpyrrolidin-3-amine수율 81.7%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of 30.6 g (0.1 mol) of [R]-2-[1-(phenylmethyl)-3-pyrrolidinyl]-1H-isoindole-1,3(2H)-dione in 300 ml of methanol was treated with 6.4 g (0.2 mol) of hydrazine. The reaction was stirred at room temperature for 18 hours and treated with 12.5 ml (0.15 mol) of concentrated hydrochloric acid. The solid was removed by filtration; the precipitate was washed with ethanol and the filtrate evaporated in vacuo. The residue was dissolved in water, made basic with 20% sodium hydroxide saturated with sodium chloride and extracted with ether (3×250 ml). The combined ether layers were washed with saturated sodium chloride solution, dried (MgSO4), filtered and evaporated in vacuo. The residue was distilled in high vacuo to give 14.4 g of the title compound, bp 86°-87°/0.15 mm.

후처리

  1. customThe solid was removed by filtration
  2. washthe precipitate was washed with ethanol
  3. customthe filtrate evaporated in vacuo
  4. dissolutionThe residue was dissolved in water
  5. extractionextracted with ether (3×250 ml)
  6. washThe combined ether layers were washed with saturated sodium chloride solution
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. distillationThe residue was distilled in high vacuo

출처 및 근거

ORD 기록
ord-61554d553e0145c7ba34cda62cf1017e
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04851418

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