Acetic Acid → HCID 19004210, compound

HRID 2225440Notes

Reaction equation

HRID 2225440 reaction equation
C([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][O:14][CH:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:9]1)C1C=CC=CC=1.C(O)(=O)C>C(O)C.[Pd]>[C:16]1([CH:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[O:14][CH2:13][CH:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 19004205HCID 19004205, compound

Product 1

HCID 19004210HCID 19004210, compoundYield 78.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-benzyl-3-(diphenylmethoxymethyl)pyrrolidine (1.43 g, Preparation 8) in ethanol (50 ml) containing acetic acid (1.0 ml) was stirred at room temperature for six days under an atmosphere of hydrogen in the presence of 5% palladium on charcoal. The mixture was filtered and the filtrate was diluted with ethyl acetate, washed with 10% aqueous sodium carbonate solution and water, dried over magnesium sulphate and evaporated to give the title compound (0.84 g) as a pale yellow oil which was characterised by its 1H-NMR spectrum.

Workup

  1. filtrationThe mixture was filtered
  2. additionthe filtrate was diluted with ethyl acetate
  3. washwashed with 10% aqueous sodium carbonate solution and water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-eaed064fd9b140d98d9315e3fcceba76
Source dataset
uspto-grants-1994_09
Patent number
US05344835

Reaction notes

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