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

HRID 1916526Notes

Reaction equation

HRID 1916526 reaction equation
Br[C:2]1[CH:13]=[CH:12][C:5]([CH2:6][N:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[CH2:14]([OH:17])[C:15]#[CH:16].C(NC(C)C)(C)C>C(#N)C.[Cu]I>[N:7]1([CH2:6][C:5]2[CH:12]=[CH:13][C:2]([C:16]#[C:15][CH2:14][OH:17])=[CH:3][CH:4]=2)[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

6

Reactant 3

HCID 7859Propargyl alcoholHCID 7912DiisopropylamineHCID 127380041-(4-Bromobenzyl)pyrrolidine

Product 1

HCID 615390893-(4-Pyrrolidin-1-ylmethyl-phenyl)-prop-2-yn-1-ol

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4.8 g (20.0 mmol) 1-(4-bromo-benzyl)-pyrrolidine, 1.75 mL (30.0 mmol) propargylalcohol, 2.31 g (2.0 mmol) tetrakis-triphenylphosphane-palladium, 381 mg (2.0 mmol) CuI and 7.07 mL diisopropylamine in 100 mL acetonitrile is heated for 14 h at 60° C. under an argon atmosphere. The solvent is distilled off i.vac., the residue is taken up in water, exhaustively extracted with EtOAc and the organic phase is dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified on silica gel (EtOAc/MeOH/NH3 95:5:0.5).

Workup

  1. distillationThe solvent is distilled off i.vac
  2. extractionexhaustively extracted with EtOAc
  3. dry with materialthe organic phase is dried over Na2SO4
  4. customis purified on silica gel (EtOAc/MeOH/NH3 95:5:0.5)

Sources & evidence

ORD record
ord-52aba8d48c0143dcb0ebec0b175dec66
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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