Isopropyl iodide → HCID 56850328, compound

HRID 2063190Notes

Reaction equation

HRID 2063190 reaction equation
[C:1]12([C:14]([OH:16])=[O:15])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][C:3]([C:11]([OH:13])=[O:12])([CH2:4]3)[CH2:2]1)[CH2:8]2.I[CH:18]([CH3:20])[CH3:19].N1(C2CCCCCCCCCC2)CCCN=CCC[CH2:24][CH2:23][CH2:22]1>C(#N)C.C(OCC)(=O)C>[C:1]12([C:14]([O:16][CH:23]([CH3:24])[CH3:22])=[O:15])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][C:3]([C:11]([O:13][CH:18]([CH3:20])[CH3:19])=[O:12])([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

6

Reactant 3

HCID 6362Isopropyl iodideHCID 643391,3-Adamantanedicarboxylic acidHCID 1296629601,8-Diazabicycloundec-7ene

Product 1

HCID 56850328HCID 56850328, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Diisopropyl 1,3-adamantanedicarboxylate is prepared by way of the following procedure. A 50 mL round bottom flask equipped with magnetic stir bar is charged with 1,3-admantanedicarboxylic acid (2.76 g, 12.3 mmol), 2-iodopropane (3.07 mL, 30.8 mmol) and 1,8-diazabicycloundec-7-ene (4.60 mL, 30.8 mmol) in 25 mL acetonitrile. The mixture is heated to reflux overnight and cooled to room temperature. The reaction is diluted with 100 mL of ethyl acetate and washed with saturated NH4Cl/1N HCl, water, saturated sodium bicarbonate, and then brine. The organic layer is dried over sodium sulfate. After filtration, the filtrate is concentrated, and the residue is dried in vacuo. The crude product is further purified by distillation in vacuo to yield the product as a white liquid.

Workup

  1. customA 50 mL round bottom flask equipped with magnetic stir bar
  2. temperatureThe mixture is heated
  3. temperatureto reflux overnight
  4. washwashed with saturated NH4Cl/1N HCl, water, saturated sodium bicarbonate
  5. dry with materialThe organic layer is dried over sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate is concentrated
  8. customthe residue is dried in vacuo
  9. distillationThe crude product is further purified by distillation in vacuo

Sources & evidence

ORD record
ord-3acd8762fb0943cbba203467f9b7dcba
Source dataset
uspto-grants-2012_10
Patent number
US08288304B2

Reaction notes

Loading…