HCID 13423950, compound → HCID 13423951, compound

HRID 1980248Notes

Reaction equation

HRID 1980248 reaction equation
C([N:8]1[CH2:12][CH2:11][C:10]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH2:23][CH3:24])([OH:13])[CH2:9]1)C1C=CC=CC=1>C(O)C.[Pd]>[CH2:23]([O:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[O:15][CH2:14][C:10]1([OH:13])[CH2:11][CH2:12][NH:8][CH2:9]1)[CH3:24]

Participants

4

Reactant 1

HCID 13423950HCID 13423950, compound

Product 1

HCID 13423951HCID 13423951, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 10.0 g (0.0305 mole) of 1-benzyl-3-(2-ethoxyphenoxy)methyl-3-pyrrolidinol in 125 ml of absolute ethanol was treated with Pd/C catalyst and warmed while shaking under a hydrogen atmosphere on a Parr hydrogenation apparatus for 16 hours. The catalyst was removed by filtration and the filtrate evaporated under reduced pressure. The white crystalline residue (7.1 g) was recrystallized from benzene isooctane to yield 6.6 g of product (91%), m.p. 108°-110° C.

Workup

  1. temperaturewarmed
  2. customThe catalyst was removed by filtration
  3. customthe filtrate evaporated under reduced pressure
  4. customThe white crystalline residue (7.1 g) was recrystallized from benzene isooctane

Sources & evidence

ORD record
ord-542dd287f1774dedb2e81c61ad093770
Source dataset
uspto-grants-1985_04
Patent number
US04508724

Reaction notes

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