Triphenylphosphine → HCID 11978976, compound

HRID 657628Notes

Reaction equation

HRID 657628 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[C:30]1([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH2:31]1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1(C)C=CC=CC=1>[C:30]1([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:35]=[CH:34][C:33]([O:1][CH2:2][CH2:3][CH2:4][N:5]2[CH2:9][CH2:8][CH2:7][CH2:6]2)=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 2093421-PyrrolidinepropanolHCID 19747111HCID 19747111, compound

Product 1

HCID 11978976HCID 11978976, compoundYield 59.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-(3-hydroxypropyl)pyrrolidine (400 mg), triphenylphosphine (812 mg) in toluene (18 mL) is stirred for five minutes at room temperature, 1-hydroxybiphenyl (493 mg) is then added. The mixture is cooled and diisopropyl azodicarboxylate (609 μL) is added. The mixture is stirred for 48 hours room temperature, concentrated under reduced pressure and diluted with ethyl acetate. The organic layer is washed with water and extracted with an aqueous 1N hydrochloric solution. The aqueous phase is washed with ethyl acetate, then made alkaline with an aqueous 5N sodium hydroxide solution and extracted twice with ethyl acetate. These extracts are pooled, dried over magnesium sulphate, concentrated under reduced pressure, diluted with diethyl oxide and mixed with a solution of oxalic acid (169 mg) dissolved in acetone. The precipitate is filtered, washed with diethyl oxide and dried to give 480 mg of 1-{3-[(biphenyl-4-yl)oxy]propyl}pyrrolidine, oxalate as a white solid melting at 201° C.

Workup

  1. temperatureThe mixture is cooled
  2. stirringThe mixture is stirred for 48 hours room temperature
  3. concentrationconcentrated under reduced pressure
  4. additiondiluted with ethyl acetate
  5. washThe organic layer is washed with water
  6. extractionextracted with an aqueous 1N hydrochloric solution
  7. washThe aqueous phase is washed with ethyl acetate
  8. extractionextracted twice with ethyl acetate
  9. dry with materialdried over magnesium sulphate
  10. concentrationconcentrated under reduced pressure
  11. additiondiluted with diethyl oxide
  12. additionmixed with a solution of oxalic acid (169 mg)
  13. dissolutiondissolved in acetone
  14. filtrationThe precipitate is filtered
  15. washwashed with diethyl oxide
  16. customdried

Sources & evidence

ORD record
ord-2260cbdca2e14ca7975e63020cfdd49e
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

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