1-Bromopropane → HCID 59550052, compound

HRID 2063191Notes

Reaction equation

HRID 2063191 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.Br[CH2:18][CH2:19][CH3:20].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][CH2:22][CH2:23][CH3:24])=[O:15])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][C:3]([C:11]([O:13][CH2:18][CH2:19][CH3:20])=[O:12])([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

6

Reactant 3

HCID 78401-BromopropaneHCID 643391,3-Adamantanedicarboxylic acidHCID 1296629601,8-Diazabicycloundec-7ene

Product 1

HCID 59550052HCID 59550052, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Di-n-propyl 1,3-adamantanedicarboxylate is prepared by way of the following procedure. A 50 mL round bottom flask equipped with a magnetic stir bar is charged with 1,3-admantanedicarboxylic acid (3.36 g, 15.0 mmol), 1-bromopropane (3.28 mL, 36.0 mmol) and 1,8-diazabicycloundec-7-ene (5.38 mL, 36.0 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 a 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-7f636379821c42b1a8c232191667ce57
Source dataset
uspto-grants-2012_10
Patent number
US08288304B2

Reaction notes

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