1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 10935011, compound

HRID 989509Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:12][CH2:11][CH2:10][CH:9]2[NH2:13])[CH:5]=[CH:6][CH:7]=1.C1CCN2C(=NCCC2)CC1.[CH:25]([S:28](Cl)(=[O:30])=[O:29])([CH3:27])[CH3:26]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([C@H:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[NH:13][S:28]([CH:25]([CH3:27])[CH3:26])(=[O:30])=[O:29])[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A 100 mL round bottom flask equipped with a magnetic stirrer was charged with (+,−) cis-[2-(3-fluoro-phenyl)-cyclopentylamine (650 mg, 3.63 mmol) from preparation 14, methylene chloride (15.0 mL) and the solution cooled to 0° C. DBU (0.65 mL, 4.35 mmol) and isopropylsulfonyl chloride (0.49 mL, 4.35 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 573 mg (55%) of the purified title compound as a white solid. 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 573 mg (55%) of the
custompurified title compound as a white solid

Sources & evidence

ORD record: ord-41989895c56c4ec08a129e98cc695dc2
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06639107B1

Reaction notes

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