1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 69112697, compound
Reaction equation
[F:1][C:2]1[CH:3]=[C:4](C2CCCC2N)C=[C:6]([F:8])[CH:7]=1.[CH2:15]1[CH2:25][CH2:24][N:23]2[C:18](=NCCC2)[CH2:17][CH2:16]1.[CH:26]([S:29](Cl)(=[O:31])=[O:30])([CH3:28])[CH3:27]>C(Cl)Cl>[F:8][C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:18]=1[C@H:17]1[CH2:16][CH2:15][CH2:25][C@H:24]1[NH:23][S:29]([CH:26]([CH3:28])[CH3:27])(=[O:31])=[O:30]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A 100 mL round bottom flask equipped with a magnetic stirrer was charged with (+,−) cis-[2-(3,5-difluoro-phenyl)-cyclopentylamine (83 mg, 0.42 mmol), methylene chloride (5.0 mL) and the solution cooled to 0° C. DBU (0.08 mL, 0.51 mmol) and isopropylsulfonyl chloride (0.06 mL, 0.51 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 83 mg (65%) 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 83 mg (65%) of the
- custompurified title compound
Sources & evidence
- ORD record
- ord-535334d5c1a64e3c9157f10a5b6cd32d
- Source dataset
- uspto-grants-2003_10
- Patent number
- US06639107B1
Reaction notes
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