Water → (2-Oxo-4-propylpyrrolidin-1-yl)methyl diethylcarbamate

HRID 2358245Notes

Reaction equation

HRID 2358245 reaction equation
[OH:1][CH2:2][N:3]1[CH2:7][CH:6]([CH2:8][CH2:9][CH3:10])[CH2:5][C:4]1=[O:11].C(N(CC)CC)C.[CH2:19]([N:21]([CH2:25][CH3:26])[C:22](Cl)=[O:23])[CH3:20].O>ClCCl>[CH2:19]([N:21]([CH2:25][CH3:26])[C:22](=[O:23])[O:1][CH2:2][N:3]1[CH2:7][CH:6]([CH2:8][CH2:9][CH3:10])[CH2:5][C:4]1=[O:11])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 6916Diethylcarbamoyl chlorideHCID 8471TriethylamineHCID 113326021-(Hydroxymethyl)-4-propylpyrrolidin-2-one

Product 1

HCID 11448237(2-Oxo-4-propylpyrrolidin-1-yl)methyl diethylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 1-(hydroxymethyl)-4-propyl-pyrrolidin-2-one a24 (4 g, 25.44 mmol) and triethylamine (1.2 eq, 30.53 mmol, 3.089 g; 4.26 ml) in 25 ml of dichloromethane was added dropwise a solution of diethylcarbamyl chloride (1.1 eq, 27.99 mmol, 3.795 g, 3.55 ml) in dichloromethane (5 ml) at room temperature. The crude mixture was allowed to react under agitation and inert atmosphere overnight. Hydrolysis (15 ml of water), extraction (CH2Cl2), drying of the combinated organic layers (MgSO4), filtration and solvent evaporation under reduced pressure gave (2-oxo-4-propylpyrrolidin-1-yl)methyl diethylcarbamate a26 (100%) which was used without any further purification.

Workup

  1. customto react under agitation and inert atmosphere overnight
  2. dry with materialdrying of the combinated organic layers (MgSO4), filtration and solvent evaporation under reduced pressure

Sources & evidence

ORD record
ord-5582d3ecddf24368a6ced949e58ecaeb
Source dataset
uspto-grants-2010_07
Patent number
US07763644B2

Reaction notes

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