Dimethylformamide → 1-Benzyl-3-(2-propynyloxy)pyrrolidine

HRID 2216361Notes

Reaction equation

HRID 2216361 reaction equation
[H-].[Na+].[CH2:3]([N:10]1[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CN(C)C=O.[CH2:21](Br)[C:22]#[CH:23]>C(OCC)(=O)C.O>[CH2:3]([N:10]1[CH2:14][CH2:13][CH:12]([O:15][CH2:23][C:22]#[CH:21])[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 69889N-benzyl-3-pyrrolidinol

Product 1

HCID 219422551-Benzyl-3-(2-propynyloxy)pyrrolidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

On an ice bath, 233 mg of sodium hydride was added to a mixture of 948 mg of 1-benzyl-3-pyrrolidinol and 10 ml of N,N-dimethylformamide and the mixture was stirred at room temperature for 1 hour. There action mixture was cooled to −40° C. and 495 μl of propargyl bromide was added thereto. The temperature was elevated to room temperature and water and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed with water and brine, dried over anhydrous magnesium sulfate and the solvent was removed. The residue was purified by NH-silica gel column chromatography with 15% ethyl acetate/hexane, to give 507 mg of the title compound.

Workup

  1. temperatureThere action mixture was cooled to −40° C.
  2. customwas elevated to room temperature
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed
  7. customThe residue was purified by NH-silica gel column chromatography with 15% ethyl acetate/hexane

Sources & evidence

ORD record
ord-0ddcbeb191ea4b0fb5f4554db4ad5174
Source dataset
uspto-grants-2006_09
Patent number
US07112593B2

Reaction notes

Loading…