1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 10967953, compound

HRID 989504Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

A 100 mL round bottom flask equipped with a magnetic stirrer is charged with (+,−) cis-2-p-tolyl-cyclopentylamine (313 mg, 1.79 mmol, from preparation 9), methylene chloride (5.0 mL) and the solution cooled to 0° C. DBU (0.32 mL, 2.14 mmol) and isopropylsulfonyl chloride (0.24 mL, 2.14 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 aqueous ammonium chloride, brine and the organic layer dried over sodium sulfate. The title compound was purified by radial chromatography eluting with methylene chloride to give 250 mg (50%) of the purified title compound.

Workup

customA 100 mL round bottom flask equipped with a magnetic stirrer
custombrought to room temperature
stirringwith stirring overnight
washwashed with aqueous ammonium chloride, brine
dry with materialthe organic layer dried over sodium sulfate
customThe title compound was purified by radial chromatography
washeluting with methylene chloride
customto give 250 mg (50%) of the
custompurified title compound

Sources & evidence

ORD record: ord-e79a6f3e4dd246c4954c018403aaac8d
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06639107B1

Reaction notes

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