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

HRID 1241514ノート

反応式

HRID 1241514 の反応式
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

参加物

5

反応物 3

HCID 31268Pyrrolidine2 回HCID 82241Magnesium Bromide2 回HCID 10487446Methyl 3,3-dimethoxycyclobutane-1-carboxylate

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-82086d54b17740dfbe0667c06467bf46
出典データセット
uspto-grants-2006_10
特許番号
US07115600B2

反応ノート

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