Methyl 1-benzyl-5-oxopyrrolidine-3-carboxylate → Methyl 1-benzylpyrrolidine-3-carboxylate

HRID 654519

반응식

HRID 654519 반응식
[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]([O:15][CH3:16])=[O:14])[CH2:10][C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.C1COCC1.Cl.CO>C1COCC1>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]([C:13]([O:15][CH3:16])=[O:14])[CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 98909Methyl 1-benzyl-5-oxopyrrolidine-3-carboxylateHCID 2723981Borane;tetrahydrofuranHCID 21893726Hydrochloride methanol

생성물 1

HCID 4610751Methyl 1-benzylpyrrolidine-3-carboxylate수율 50.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of methyl 1-benzyl-2-oxo-4-pyrrolidylcarboxylate (D10, 35.4 g, 0.18 mole) in dry THF (135 ml) was added dropwise over 30 mins to 1M borane-THF solution (228 ml, 0.23 mole) at 0° C. under nitrogen, and when addition was complete the solution was heated under reflux for 1h. The solution was cooled to room temperature, then treated dropwise with 8% hydrogen chloride/methanol (114 ml, 0.25 mole HCl) and stirred for 18h, followed by 3h at reflux. The mixture was then concentrated in vacuo and the residue treated with water (40 ml), washed with ether (2×50 ml), basified with 40% sodium hydroxide solution, saturated with potassium carbonate and extracted with ether (3×70 ml). The combined extracts were dried (Na2SO4) and concentrated in vacuo to leave a yellow oil, which was purified by distillation (b.p. 146° C.0.7mm) to give the title compound (D11) as a colourless oil (19.8 g, 50%).

후처리

  1. additionwhen addition
  2. temperaturewas heated
  3. temperatureunder reflux for 1h
  4. temperatureat reflux
  5. concentrationThe mixture was then concentrated in vacuo
  6. additionthe residue treated with water (40 ml)
  7. washwashed with ether (2×50 ml)
  8. extractionextracted with ether (3×70 ml)
  9. dry with materialThe combined extracts were dried (Na2SO4)
  10. concentrationconcentrated in vacuo
  11. customto leave a yellow oil, which
  12. distillationwas purified by distillation (b.p. 146° C.0.7mm)

출처 및 근거

ORD 기록
ord-d7fce74ab2f8417f9631c77014014c0e
출처 데이터셋
uspto-grants-1992_07
특허 번호
US05132316

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