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

HRID 989496Notes

Reaction equation

[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

Participants

Conditions

Temperature: 0 °C

Procedure

(+,−) 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.

Workup

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

Sources & evidence

ORD record: ord-41391b6d4e0d4dcea3f489f66926d32b
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06639107B1

Reaction notes

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