Tetrahydrofuran → 8-(1,2-Dihydroxy-ethyl)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 61759Notes

Reaction equation

HRID 61759 reaction equation
[CH2:1]1[CH2:5][O:4][CH2:3][CH2:2]1.[CH3:6][C:7]1([CH3:29])[C:19]2[NH:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:20]#[N:21])[CH:16]=3)[C:11]=2[C:10](=[O:22])[C:9]2[CH:23]=[CH:24]C(C=C)=C[C:8]1=2.C[N+]1([O-])CC[O:34]CC1.C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O.[Na].[Na]>[Os](=O)(=O)(=O)=O.C(O)(C)(C)C>[OH:34][CH:1]([C:2]1[CH:24]=[CH:23][C:9]2[C:10](=[O:22])[C:11]3[C:12]4[C:17](=[CH:16][C:15]([C:20]#[N:21])=[CH:14][CH:13]=4)[NH:18][C:19]=3[C:7]([CH3:6])([CH3:29])[C:8]=2[CH:3]=1)[CH2:5][OH:4]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 82029Methyl morpholine oxideHCID 9949814Ethylenediaminetetraacetic acid disodiumHCID 668340546,6-Dimethyl-11-oxo-8-vinyl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

Product 1

HCID 668343198-(1,2-Dihydroxy-ethyl)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrileYield 63%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 6386tert-ButanolSolvent

Procedure

To the THF (1 ml) solution of 6,6-dimethyl-11-oxo-8-vinyl-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound B2-24, 20 mg, 0.064 mmol), t-butanol solution of osmium tetraoxide (19 μl, 0.3 eq.) and 50% aqueous solution of N-methylmorpholine-N-oxide (30 μl, 2.0 eq.) were added and the mixture was stirred at room temperature for 3 hr. To the reaction solution, 10% aqueous solution of disodium ethylenediamine tetraacetic acid was added, followed by extraction with ethyl acetate. The organic layer was dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were purified by high performance liquid chromatography to obtain the title compound (21 mg, 63%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customThe drying agent was removed by filtration
  4. customthe residues obtained
  5. concentrationafter concentration under reduced pressure
  6. customwere purified by high performance liquid chromatography

Sources & evidence

ORD record
ord-03b2809b6fa64788afce4cfbaaeacb88
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Reaction notes

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