Hydrochloric Acid → Methyl 1-benzylpyrrolidine-3-carboxylate

HRID 489915

반응식

HRID 489915 반응식
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][C:8](=O)[N:7]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:6]1)=[O:4].B.O1CCCC1.Cl>O1CCCC1>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][N:7]([CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:6]1)=[O:4]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 98909Methyl 1-benzyl-5-oxopyrrolidine-3-carboxylateHCID 2723981Borane;tetrahydrofuran

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 1-benzyl-5-oxo-pyrrolidine-3-carboxylic acid methyl ester (30 mmol, 7 g) in anhydrous tetrahydrofuran (40 ml) was added borane-tetrahydrofuran solution (1M, 50 mmol, 50 mL) at ambient temperature. When gas evolution had subsided the solution was heated under reflux for 75 min then stirred for 16 hr at ambient temperature. Hydrochloric acid (6M) was added dropwise (ca. 5 mL) and the mixture was stirred at ambient temperature for 1 hr before removing the solvent under vacuum. The residue was dissolved in dichloromethane and the solution was washed with dilute sodium hydroxide solution. The dichloromethane solution was then extracted with dilute hydrochloric acid (×3), the extracts combined, made basic by addition of sodium hydroxide and extracted with dichloromethane (×3). The combined organic extract was dried over anhydrous sodium sulfate and the solvent was removed under vacuum. The product was purified by chromatography on silica gel eluting with 5% methanol-dichloromethane to give 1-benzyl-pyrrolidine-3-carboxylic acid methyl ester (200 mg, 3%).

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 75 min
  3. stirringthe mixture was stirred at ambient temperature for 1 hr
  4. custombefore removing the solvent under vacuum
  5. dissolutionThe residue was dissolved in dichloromethane
  6. washthe solution was washed with dilute sodium hydroxide solution
  7. extractionThe dichloromethane solution was then extracted with dilute hydrochloric acid (×3)
  8. additionmade basic by addition of sodium hydroxide
  9. extractionextracted with dichloromethane (×3)
  10. extractionThe combined organic extract
  11. dry with materialwas dried over anhydrous sodium sulfate
  12. customthe solvent was removed under vacuum
  13. customThe product was purified by chromatography on silica gel eluting with 5% methanol-dichloromethane

출처 및 근거

ORD 기록
ord-03eb48fd686e4482bb584f621892f2eb
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06979741B2

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