1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 11121532, compound

HRID 989506Notes

Reaction equation

C(O)(=O)C(O)=O.[Br:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:18][CH2:17][CH2:16][CH:15]2[NH2:19])=[CH:10][CH:9]=1.C1CCN2C(=NCCC2)CC1.[CH:31]([S:34](Cl)(=[O:36])=[O:35])([CH3:33])[CH3:32]>C(Cl)Cl>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([C@H:14]2[CH2:18][CH2:17][CH2:16][C@H:15]2[NH:19][S:34]([CH:31]([CH3:33])[CH3:32])(=[O:36])=[O:35])=[CH:12][CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A 100 mL round bottom flask equipped with a magnetic stirrer was charged with (+,−) cis-[2-(4-bromo-phenyl)-cyclopentylamine oxalate salt (500 mg, 1.51 mmol), methylene chloride (5.0 mL) and the solution was cooled to 0° C. DBU (1.8 mL, 12.1 mmol) and isopropylsulfonyl chloride (1.02 mL, 9.06 mmol) were added. The reaction was then stirred at 0° C. for 60.0 minutes and brought to room temperature with stirring overnight. The reaction was diluted with methylene chloride and washed with 1N HCl, brine and the organic layer dried over sodium sulfate. The title compound was purified by radial chromatography eluting with methylene chloride to give 233 mg (45%) of the purified title compound. The nmr was consistent with the assigned structure.

Workup

customA 100 mL round bottom flask equipped with a magnetic stirrer
custombrought to room temperature
stirringwith stirring overnight
washwashed with 1N HCl, brine
dry with materialthe organic layer dried over sodium sulfate
customThe title compound was purified by radial chromatography
washeluting with methylene chloride
customto give 233 mg (45%) of the
custompurified title compound

Sources & evidence

ORD record: ord-7d74cf315cc84feaa896a428c18db05a
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06639107B1

Reaction notes

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