HCID 23036274, compound → HCID 23036262, compound

HRID 1709864Notes

Reaction equation

HRID 1709864 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)([CH:10]2[CH2:14][CH2:13][N:12](CC3C=CC=CC=3)[CH2:11]2)[OH:9])=[CH:4][CH:3]=1>C(O)C.[Pd]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:22]2[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)([CH:10]2[CH2:14][CH2:13][NH:12][CH2:11]2)[OH:9])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 23036274HCID 23036274, compound

Product 1

HCID 23036262HCID 23036262, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 26.6 g (0.07 mole) of α,α-bis(4-fluorophenyl)-1-(phenylmethyl)-3-pyrrolidinemethanol in 500 ml of ethanol was hydrogenated at 60 psi and 70° C. over 5% palladium on carbon catalyst for 2 days. The mixture was cooled and filtered through Celite®. The filtrate was concentrated under reduced pressure to give a solid as residue. The solid was triturated with petroleum ether (30°-60° C.), collected by filtration and dried to yield 18.5 g (91%) of the title compound as a white solid, m.p. 152°-153° C. (2-propanol).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered through Celite®
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customto give a solid as residue
  5. customThe solid was triturated with petroleum ether (30°-60° C.)
  6. filtrationcollected by filtration
  7. customdried

Sources & evidence

ORD record
ord-964b027f1e094bb99f6afdb223a82ef1
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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