1,8-Diazabicyclo(5.4.0)undec-7-ene → cis-[(Methylethyl)sulfonyl](2-phenylcyclopentyl)amine

HRID 989496노트

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HRID 989496 반응식
[C:1]1([C@H:7]2[CH2:11][CH2:10][CH2:9][C@H:8]2[NH2:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1CCN2C(=NCCC2)CC1.[CH:24]([S:27](Cl)(=[O:29])=[O:28])([CH3:26])[CH3:25]>C(Cl)Cl>[C:1]1([C@H:7]2[CH2:11][CH2:10][CH2:9][C@H:8]2[NH:12][S:27]([CH:24]([CH3:26])[CH3:25])(=[O:29])=[O:28])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

5

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 824082-Propanesulfonyl chlorideHCID 10931745Cyclopentanamine, 2-phenyl-, (1R,2R)-rel-

생성물 1

HCID 11119059cis-[(Methylethyl)sulfonyl](2-phenylcyclopentyl)amine수율 27%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

(+,−) Cis-2-Phenyl-cyclopentylamine (0.43 g, 2.7 mmol, from preparations 5 or 7) was dissolved in 15 mL of methylene chloride and cooled to 0° C. under nitrogen. 0.52 mL (3.5 mmol) of DBU was added followed by 0.39 mL (3.5 mmol) of isopropylsulfonyl chloride. Stirring was allowed to continue for 3 days while warming to room temperature. The reaction was washed with 1N HCl and the organic phase dried over sodium sulfate. Filtered, and concentrated in vacuo to a crude brown solid which was a 4:1 mixture of cis:trans by NMR. The isomers were purified by radial chromatography eluting with methylene chloride. 195 mg (27%) of the title compound (cis isomer) was isolated as a white solid as well as 15 mg of the more polar trans isomer. The NMR was consistent with the assigned structure.

후처리

  1. temperaturewhile warming to room temperature
  2. washThe reaction was washed with 1N HCl
  3. dry with materialthe organic phase dried over sodium sulfate
  4. filtrationFiltered
  5. concentrationconcentrated in vacuo to a crude brown solid which
  6. additiona 4:1 mixture of cis
  7. customThe isomers were purified by radial chromatography
  8. washeluting with methylene chloride

출처 및 근거

ORD 기록
ord-41391b6d4e0d4dcea3f489f66926d32b
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06639107B1

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