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

HRID 232050

反応式

HRID 232050 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 1519354(3R)-1-benzylpyrrolidin-3-amine収率 81.7%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-61554d553e0145c7ba34cda62cf1017e
出典データセット
uspto-grants-1989_07
特許番号
US04851418

関連ノート

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