HCID 18643898, compound → HCID 20067703, compound

HRID 982441Notes

Reaction equation

HRID 982441 reaction equation
[Cl:1][CH2:2][CH2:3]/[C:4](/[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[C:5](\[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)/[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:8][CH:7]=1.[H][H]>[Pd].C(O)(=O)C>[Cl:1][CH2:2][CH2:3][CH:4]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH:5]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:13][CH2:14][N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 18643898HCID 18643898, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20067703HCID 20067703, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

(RR, SS)-isomers: A mixture containing 43.2 g of (Z)-4-chloro-1,2-diphenyl-1-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]-1-butene, 4 g of 5% palladium-on-charcoal and 800 ml of glacial acetic acid is stirred under hydrogen atmosphere at 75° C. until one equivalent of hydrogen is consumed, about 6 h. The solvent is evaporated and the evaporation residue is dissolved in toluene. The toluene solution is washed first with 2 M sodium hydroxide solution and then with water, after which the solution is dried over sodium sulfate. Finally the solvent is evaporated leaving the product as an oil at quantitative yield.

Workup

  1. customis consumed, about 6 h
  2. customThe solvent is evaporated
  3. dissolutionthe evaporation residue is dissolved in toluene
  4. washThe toluene solution is washed first with 2 M sodium hydroxide solution
  5. dry with materialwith water, after which the solution is dried over sodium sulfate
  6. customFinally the solvent is evaporated

Sources & evidence

ORD record
ord-d64b55ddba4e41278fb690a895cd5bd2
Source dataset
uspto-grants-1991_02
Patent number
US04996225

Reaction notes

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