Potassium Carbonate → 1-(4-But-3-ynyl-benzyl)-pyrrolidine

HRID 1916529Notes

Reaction equation

HRID 1916529 reaction equation
[N+](=[C:3](P(=O)(OC)OC)C(=O)C)=[N-].[N:13]1([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH:27]=O)=[CH:21][CH:20]=2)[CH2:17][CH2:16][CH2:15][CH2:14]1.C([O-])([O-])=O.[K+].[K+]>CO.C(OCC)C>[CH2:25]([C:22]1[CH:23]=[CH:24][C:19]([CH2:18][N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:20][CH:21]=1)[CH2:26][C:27]#[CH:3]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 859698393-(4-Pyrrolidin-1-ylmethyl-phenyl)-propionaldehydeHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 859698431-(4-But-3-ynyl-benzyl)-pyrrolidine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

815 mg (4.2 mmol) dimethyl (1-diazo-2-oxo-propyl)-phosphonate is added to a mixture of 760 mg (3.5 mmol) 3-(4-pyrrolidin-1-ylmethyl-phenyl)-propionaldehyde and 970 mg (7.0 mmol) K2CO3 in 100 mL dry MeOH under an argon atmosphere and stirred overnight at RT. The reaction mixture is diluted with diethyl ether, the organic phase is washed with saturated, aqueous NaHCO3 solution and 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. washthe organic phase is washed with saturated, aqueous NaHCO3 solution
  2. dry with materialdried over Na2SO4
  3. customis purified on silica gel (EtOAc/MeOH/NH3 95:5:0.5)

Sources & evidence

ORD record
ord-b36d18e7802944b492ba23e99e0b4cde
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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