Water → Bis(tropan-3-yl) succinate

HRID 1603704Notes

Reaction equation

HRID 1603704 reaction equation
[CH3:1][N:2]1[CH:6]2[CH2:7][CH:8]([OH:10])[CH2:9][CH:3]1[CH2:4][CH2:5]2.[C:11](Cl)(=[O:17])[CH2:12][CH2:13][C:14](Cl)=[O:15].[OH2:19].[OH-].[Na+]>C(Cl)Cl>[C:11]([O:17][CH:8]1[CH2:7][C@H:6]2[N:2]([CH3:1])[C@H:3]([CH2:4][CH2:5]2)[CH2:9]1)(=[O:19])[CH2:12][CH2:13][C:14]([O:10][CH:8]1[CH2:9][C@H:3]2[N:2]([CH3:1])[C@H:6]([CH2:5][CH2:4]2)[CH2:7]1)=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 84248-Methyl-8-azabicyclo(3.2.1)octan-3-olHCID 10970Succinyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 11824654Bis(tropan-3-yl) succinateYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 14.1 g (100 mmol) of tropine in 50 mL of methylene chloride is added dropwise 7.75 g (50 mmol) of succinyl chloride in 100 mL of methylene chloride with cooling in an ice bath. Then the mixture is allowed to warm to room temperature. After the reaction mixture is poured into 200 mL of cold water, the aqueous layer is adjusted to pH 10-11 with 6 N NaOH aqueous solution and extracted with chloroform. The resulting oil is purified by column chromatography (silica gel, 20% methanol in chloroform) to yield 11.8 g (65%) of bis-tropan-3-yl succinate as a thick oil.

Workup

  1. temperaturewith cooling in an ice bath
  2. extractionextracted with chloroform
  3. customThe resulting oil is purified by column chromatography (silica gel, 20% methanol in chloroform)

Sources & evidence

ORD record
ord-918557ee1a684ec8941bcf81937c5f85
Source dataset
uspto-grants-1999_11
Patent number
US05990124

Reaction notes

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