Dibah → 7-(9H-Fluoren-2-yl)-7,9-diaza-bicyclo[4.2.2]dec-3-ene

HRID 40626

Reaction equation

[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1[N:14]1[C:21](=O)[CH:20]2[NH:23][C:24](=O)[CH:15]1[CH2:16][CH:17]=[CH:18][CH2:19]2.CC(C[Al]CC(C)C)C>C1COCC1.C(OCC)C>[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1[N:14]1[CH2:21][CH:20]2[NH:23][CH2:24][CH:15]1[CH2:16][CH:17]=[CH:18][CH2:19]2

Participants

Conditions

Temperature: 130 °C

Procedure

7-(9H-Fluoren-2-yl)-7,9-diaza-bicyclo[4.2.2]dec-3-ene-8,10-dione (310 mg, 0.94 mmol) in THF (4 mL) was placed in a μW tube. Dibal-H (4 mL, 4 mmol, [1M] in THF) was then added to the reaction mixture with venting under argon flow. When all H2 evolution was completed, the reaction mixture was heated to 130° C. for 900 sec. The reaction mixture was then diluted with a saturated Rochelle's solution (30 mL) and diethyl ether (30 mL) followed by stirring vigorously overnight. The layers were separated and the organic solution was dried with magnesium sulfate, filtered and the solvent removed by reduced pressure to yield the title compound as a residue.

Workup

customThe layers were separated
dry with materialthe organic solution was dried with magnesium sulfate
filtrationfiltered
customthe solvent removed by reduced pressure

Sources & evidence

ORD record: ord-8cee26150f8d4837884a2005f2ecc90d
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530475B2

Linked notes

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