Pyrrolidine → 1-[(3,3-Dimethoxycyclobutyl)carbonyl]pyrrolidine

HRID 1241514노트

반응식

HRID 1241514 반응식
CO[C:3]([CH:5]1[CH2:8][C:7]([O:11][CH3:12])([O:9][CH3:10])[CH2:6]1)=[O:4].[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.[Br-].[Mg+2].[Br-]>C(#N)C>[CH3:12][O:11][C:7]1([O:9][CH3:10])[CH2:6][CH:5]([C:3]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:4])[CH2:8]1

참가 물질

5

반응물 3

HCID 31268Pyrrolidine2회HCID 82241Magnesium Bromide2회HCID 10487446Methyl 3,3-dimethoxycyclobutane-1-carboxylate

생성물 1

HCID 219348521-[(3,3-Dimethoxycyclobutyl)carbonyl]pyrrolidine수율 86%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a stirring solution of 3,3-dimethoxy-cyclobutanecarboxylic acid methyl ester, (J. Org. Chem. 1988, 53, 3841 and J. Org. Chem. 1996, 61, 2174) (1.0 g, 5.7 mmol) in acetonitrile (200 mL) was added pyrrolidine (951 uL, 11.5 mmol), followed by magnesium bromide (0.53 g, 2.9 mmol). The reaction was then heated to 60 □C (oil bath) for 18 hours. After 18 hours a second portion of pyrrolidine (1.9 mL, 23 mmol) and magnesium bromide (0.8 g, 4.3 mmol were added. The reaction was then heated to 80 □C (oil bath) for 48 hours. TLC and MS analysis indicated complete consumption of starting material. The reaction was cooled to room temperature and quenched with a saturated solution of NaHCO3, and diluted with CH2Cl2. The layers were separated and the organic layer was dried over magnesium sulfate, filtered through a fritted funnel and concentrated under reduced pressure. Purification of this material was accomplished by flash column chromatography using a 40M Biotage column, eluting with 70% EtOAc/toluene. The product containing fractions were collected and concentrated under reduced pressure to give the title compound (1.0 g, 86% yield) as a colorless oil.

후처리

  1. temperatureThe reaction was then heated to 60 □C (oil bath) for 18 hours
  2. temperatureThe reaction was then heated to 80 □C (oil bath) for 48 hours
  3. customconsumption of starting material
  4. customquenched with a saturated solution of NaHCO3
  5. additiondiluted with CH2Cl2
  6. customThe layers were separated
  7. dry with materialthe organic layer was dried over magnesium sulfate
  8. filtrationfiltered through a fritted funnel
  9. concentrationconcentrated under reduced pressure
  10. customPurification of this material
  11. washeluting with 70% EtOAc/toluene
  12. additionThe product containing fractions
  13. customwere collected
  14. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-82086d54b17740dfbe0667c06467bf46
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07115600B2

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