Triethylamine → tert-Butyl 2-oxo-4-propyl-1-pyrrolidinecarboxylate

HRID 1453913Notes

Reaction equation

HRID 1453913 reaction equation
C(N(CC)CC)C.[C:8]([O:15]C([O-])=O)([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=O.CN(C1C=CC=CN=1)C.[CH2:28]([CH:31]1[CH2:35][NH:34][C:33](=[O:36])[CH2:32]1)[CH2:29][CH3:30]>C(Cl)Cl>[O:36]=[C:33]1[CH2:32][CH:31]([CH2:28][CH2:29][CH3:30])[CH2:35][N:34]1[C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:15]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 141781004-Propylpyrrolidin-2-oneHCID 22064466Tert-butyldicarbonate

Product 1

HCID 22928663tert-Butyl 2-oxo-4-propyl-1-pyrrolidinecarboxylateYield 61.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (81.4 ml, 10 mmol), tert-butyl dicarbonate (4.2 g, 19.2 mmol) and dimethylaminopyridine (1.18 g, 9.58 mmol) were added to a solution of 4-propyl-2-pyrrolidinone (1.22 g, 9.59 mmol) in methylene chloride (20 ml) and the mixture was stirred at room temperature for 12 hours. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (1.35 g) as a colorless oil. 1H-NMR (CDCl3) δ(ppm) 0.93 (3H, t, J=7.2 Hz), 1.28-1.50 (4H, m), 1.52 (9H, s), 2.14-2.32 (2H, m), 2.61 (1H, dd, J=15.0 Hz, 7.0 Hz), 3.30 (1H, dd, J=10.8 Hz, 7.2 Hz), 3.87 (1H, dd, J=10.8 Hz, 8.0 Hz)

Workup

  1. distillationAfter distilling off the solvent under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-40dde02bd733489eb331db95ae1d12df
Source dataset
uspto-grants-2009_01
Patent number
US07476688B2

Reaction notes

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