Ethanol → HCID 70477288, compound

HRID 1981327Notes

Reaction equation

HRID 1981327 reaction equation
[C:1]1([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:8][CH2:9][CH2:10][N:11]2[CH2:15][CH2:14][CH:13]([CH2:16][C:17]([OH:19])=[O:18])[CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)C.[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]\[C:32]([OH:34])=[O:33]>CO.[Pd]>[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]\[C:32]([OH:34])=[O:33].[C:20]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH2:9][CH2:10][N:11]2[CH2:15][CH2:14][CH:13]([CH2:16][C:17]([OH:19])=[O:18])[CH2:12]2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 444266Maleic AcidHCID 9927708HCID 9927708, compound

Product 1

HCID 70477288HCID 70477288, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 0.460 g. (1.37 mmole) of 1-(4,4-diphenyl-3-butenyl)-3-pyrrolidineacetic acid in 30 ml. of absolute ethanol was reduced, using 0.15 g. of 10% palladium-on-carbon, for 1.5 hours at ambient temperature. The mixture was filtered and concentrated. A portion of the oily residue and one equivalent of maleic acid were mixed in methanol and concentrated to yield a solid which was recrystallized from isopropanol/ether to give 1-(4,4-diphenylbutyl)-3-pyrrolidineacetic acid maleate, m.p. 85°-87° C.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. concentrationconcentrated
  4. customto yield a solid which
  5. customwas recrystallized from isopropanol/ether

Sources & evidence

ORD record
ord-9bf8ace7996a4492b218594a887f000c
Source dataset
uspto-grants-1985_04
Patent number
US04514414

Reaction notes

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