Hydrochloric Acid → cis-Pyrrolidine-3,4-diyldimethanol

HRID 1366458Notes

Reaction equation

HRID 1366458 reaction equation
C1(C[N:8]2[CH2:12][C@H:11]([CH2:13][OH:14])[C@H:10]([CH2:15][OH:16])[CH2:9]2)C=CC=CC=1.Cl>CO.[OH-].[OH-].[Pd+2]>[NH:8]1[CH2:12][C@H:11]([CH2:13][OH:14])[C@H:10]([CH2:15][OH:16])[CH2:9]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 53883141(cis-1-Benzylpyrrolidine-3,4-diyl)dimethanol

Product 1

HCID 16726851cis-Pyrrolidine-3,4-diyldimethanolYield 65.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of crude [(cis)-1-(phenylmethyl)-3,4-pyrrolidinediyl]dimethanol (2.5 g) in MeOH (50 mL) was added conc HCl (0.2 mL) followed by Pearlmans catalyst (700 mg). The resulting suspension was hydrogenated for 48 hours at 50 psi on a Parr shaker, after which time a further 700 mg of the catalyst was added. Hydrogenation for another 72 hours at 50 psi resulted in completion of the reaction. Removal of the catalyst by filtration and evaporation of the solvents under reduced pressure yielded (cis)-3,4-pyrrolidinediyldimethanol (970 mg, 7.4 mmol). LCMS: (M+H)+: Not detected.

Workup

  1. customHydrogenation for another 72 hours at 50 psi resulted in completion of the reaction
  2. customRemoval of the catalyst
  3. filtrationby filtration and evaporation of the solvents under reduced pressure

Sources & evidence

ORD record
ord-437a70d861434db5a8fdcc3694cd0c9f
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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