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

HRID 989496ノート

反応式

HRID 989496 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

(+,−) 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.

後処理

  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

出典と根拠

ORDレコード
ord-41391b6d4e0d4dcea3f489f66926d32b
出典データセット
uspto-grants-2003_10
特許番号
US06639107B1

反応ノート

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