3-(4-Pyrrolidin-1-ylmethyl-phenyl)-prop-2-yn-1-ol → 3-(4-Pyrrolidin-1-ylmethyl-phenyl)-propan-1-ol

HRID 1916527Notes

Reaction equation

HRID 1916527 reaction equation
[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]#[C:14][CH2:15][OH:16])=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>CCO.[Pd]>[N:1]1([CH2:6][C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][OH:16])=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 615390893-(4-Pyrrolidin-1-ylmethyl-phenyl)-prop-2-yn-1-olHCID 178418361HCID 178418361, compound

Product 1

HCID 673653223-(4-Pyrrolidin-1-ylmethyl-phenyl)-propan-1-ol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1.65 g (7.66 mmol) 3-(4-pyrrolidin-1-ylmethyl-phenyl)-prop-2-yn-1-ol in 20 mL EtOH is combined with 200 mg 10% Pd/C and hydrogenated in the autoclave at RT and 30 psi H2 until the theoretical uptake of hydrogen is achieved. The catalyst is suction filtered, the filtrate concentrated by evaporation and the residue is purified on silica gel (EtOAc/MeOH/NH3 90:10:1).

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate concentrated by evaporation
  3. customthe residue is purified on silica gel (EtOAc/MeOH/NH3 90:10:1)

Sources & evidence

ORD record
ord-32052be004b84210aea0c0f49242afb5
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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