1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 11402394, compound

HRID 2250307Notes

Reaction equation

HRID 2250307 reaction equation
Br[CH2:2][CH:3]1[O:7][C:6]([C:9]23[CH2:18][CH:13]4[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]4)[CH2:10]2)[CH2:16]3)([CH3:8])[O:5][C:4]1=[O:19].C1CCN2C(=NCCC2)CC1>C(OC(C)C)(C)C>[CH2:2]=[C:3]1[O:7][C:6]([C:9]23[CH2:16][CH:15]4[CH2:17][CH:11]([CH2:12][CH:13]([CH2:14]4)[CH2:18]2)[CH2:10]3)([CH3:8])[O:5][C:4]1=[O:19]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 23022609HCID 23022609, compound

Product 1

HCID 11402394HCID 11402394, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent2×

Procedure

A mixture obtained by dissolving 16.4 g of 5-bromomethyl-2-(1-adamantyl)-2-methyl-1,3-dioxolan-4-one in 80 ml of isopropyl ether was placed in a flask equipped with an agitator, a thermometer, a condenser and a dropping funnel. While cooling in an ice bath, 9.1 g (0.06 mol) of 1,8-diazabicyclo[5.4.0]-7-undecene diluted with 20 ml of isopropyl ether was added by drops into the solution over 1 hour, followed by stirring at room temperature for 2 hours. After completion of the stirring, the reaction solution was analyzed. As a result, it was found that the reaction solution contained only 1.8 g of 5-methylene-2-(1-adamantyl)-2-methyl-1,3-dioxolan-4-one (yield: 15%) and that 81% of the raw materials was decomposed into adamantyl methyl ketone.

Workup

  1. customA mixture obtained
  2. customwas placed in a flask
  3. customequipped with an agitator
  4. temperatureWhile cooling in an ice bath
  5. additionwas added by drops into the solution over 1 hour

Sources & evidence

ORD record
ord-baf7f8d9398f42dd89d5d8f5d88e6e2f
Source dataset
uspto-grants-2008_01
Patent number
US07316884B2

Reaction notes

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