1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 19793367, compound

HRID 6392Notes

Reaction equation

HRID 6392 reaction equation
[C:1]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH:6]=1)([O:3][CH3:4])=[O:2].[N+:15]([C:18]1[CH:19]=[C:20]([CH2:24][CH2:25][N+:26]([O-:28])=[O:27])[CH:21]=[CH:22][CH:23]=1)([O-:17])=[O:16].N12CCCN=C1CCCCC2>C(#N)C.C(OCC)(=O)C>[C:1]([CH:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH:6]1[CH:25]([N+:26]([O-:28])=[O:27])[CH2:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([N+:15]([O-:17])=[O:16])[CH:19]=1)([O:3][CH3:4])=[O:2]

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 3673661-Nitro-3-(2-nitroethyl)benzeneHCID 12482183Methyl 3,4-dihydronaphthalene-1-carboxylate

Product 1

HCID 19793367HCID 19793367, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2 g (10.6 mmol) of 1-carbomethoxy-3,4-dihydronaphthalene, from Step 1 of Example 46, and 2.08 g (10.6 mmol) of 2-(3-nitrophenyl)-1-nitroethane, from Step 2, in 1 mL of acetonitrile was added 0.2 mL of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). The reaction mixture was stirred at ambient temperature for 0.5 h and then diluted with ethyl acetate. The reaction mixture was washed with 2N aqueous hydrochloric acid solution. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give 3.96 g (97% yield) of the title compound as a mixture of diastereomers which was taken on without purification to the next step; MS DCl--NH3M/Z: 402 (M+NH4)+ ; 1H NMR (CDCl3) δ1.52-1.86 (1H, m), 2.1-2.35 (1H, m), 2.42-2.65 (1H, m), 2.78-3.15 (2H, m), 3.2-3.33 (1H, m), 3.38-3.55 (1H, m), 3.78-3.81 (3H, s), 3.91-4.18 (1H, m), 4.68-4.88 (1H, m), 7.12-7.42 (4H, m), 7.48-7.58 (2H, m), 8.01-8.18 (2H, m).

Workup

  1. washThe reaction mixture was washed with 2N aqueous hydrochloric acid solution
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4a42d9fa1cdc4bb59ca4fa196c120674
Source dataset
uspto-grants-1993_09
Patent number
US05248677

Reaction notes

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