1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 11724479, compound

HRID 2114044Notes

Reaction equation

HRID 2114044 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]([N:5]1[C:9]2=[N:10][CH:11]=[C:12]([Br:14])[CH:13]=[C:8]2[C:7]([CH:15]=[O:16])=[CH:6]1)=[O:4].S([CH2:28][N+:29]#[C-:30])(C1C=CC(C)=CC=1)(=O)=O.C1CCN2C(=NCCC2)CC1>COCCOC>[CH3:1][N:2]([CH3:17])[C:3]([N:5]1[C:9]2=[N:10][CH:11]=[C:12]([Br:14])[CH:13]=[C:8]2[C:7]([C:15]2[O:16][CH:30]=[N:29][CH:28]=2)=[CH:6]1)=[O:4]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 161915Tosylmethyl isocyanideHCID 59811877HCID 59811877, compound

Product 1

HCID 11724479HCID 11724479, compoundYield 29.5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

To aldehyde 20 (2.00 g, 6.75 mmol) in 1,2-dimethoxyethane (70 mL) was added tosylmethyl isocyanide (1.58 g, 8.10 mmol) followed by DBU (1.44 g, 9.46 mmol), and the reaction mixture heated at 90° C. overnight. After cooling, sorbent (HM-N, Jones Chromatography) was added and the solvent evaporated. The product was purified by silicagel chromatography using ethyl acetate:hexane (4:6) (gradient elution) to give product 21 as a light orange solid (667 mg, 29%); 1H NMR (400 MHz, CDCl3) δ 3.40-2.90 (bs, 6H), 7.32 (s, 1H), 7.86 (s, 1H), 7.96 (s, 1H), 8.32 (d, J=2.2 Hz, 1H), 8.48 (d, J=2.2 Hz, 1H).

Workup

  1. temperatureAfter cooling
  2. additionsorbent (HM-N, Jones Chromatography) was added
  3. customthe solvent evaporated
  4. customThe product was purified by silicagel chromatography

Sources & evidence

ORD record
ord-c1a3869a0bd94e009634395670c7e4fa
Source dataset
uspto-grants-2008_10
Patent number
US07432375B2

Reaction notes

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