1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 11481289, compound

HRID 2261036Notes

Reaction equation

HRID 2261036 reaction equation
[C:1]([O:4][CH:5]1[CH:10](Br)[CH2:9][CH2:8][N:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:6]1)(=[O:3])[CH3:2].C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1>[C:1]([O:4][CH:5]1[CH2:6][N:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:8][CH:9]=[CH:10]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 12414167HCID 12414167, compound

Product 1

HCID 11481289HCID 11481289, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of Compound 239A (371 mmol) and DBU (92 g, 604 mmol) was heated to 90-110° C. for 30 min. After cooling to room temperature, the mixture was diluted with toluene and stirred for an additional 30 min. The precipitate was removed by filtration and rinsed with toluene. Combined filtrates were washed with 1.0 N HCl, water and dried over anhydrous anhydrous MgSO4. Concentration in vacuo afforded 67.56 g (yield: 85.4%) of 239B as an oil. 1H-NMR (400 MHz, CDCl3): 6.00 (bs, 1H), 5.90 (bs, 1H), 5.20 (m, 1H), 4.20 (q, J=7.08, 2H), 4.19 (m, 1H), 3.85 (m, 1H), 3.80 (m, 1H), 3.55 (m, 1H), 2.08 (s, 3H), 1.28 (t, J=7.08, 3H).

Workup

  1. temperatureAfter cooling to room temperature
  2. customThe precipitate was removed by filtration
  3. washrinsed with toluene
  4. washCombined filtrates were washed with 1.0 N HCl, water
  5. dry with materialdried over anhydrous anhydrous MgSO4
  6. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-6f9a1a71706f4dbea67ea0cf74bed36c
Source dataset
uspto-grants-2010_12
Patent number
US07846931B2

Reaction notes

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