Potassium Carbonate → 3-[1-Ethyl-2-pyrrolidinyl]phenyl methylcarbamate

HRID 233029Notes

Reaction equation

HRID 233029 reaction equation
[CH2:1]([N:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[C:8]1[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1)[CH3:2].[CH3:15][N:16]=[C:17]=[O:18].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH3:15][NH:16][C:17](=[O:18])[O:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([CH:4]2[CH2:5][CH2:6][CH2:7][N:3]2[CH2:1][CH3:2])[CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12228Methyl IsocyanateHCID 233613123-[1-Ethyl-2-pyrrolidinyl]phenol

Product 1

HCID 152227983-[1-Ethyl-2-pyrrolidinyl]phenyl methylcarbamateYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[1-ethyl-2-pyrrolidinyl]phenol (0.8 g) in dry tetrahydrofuran (40 ml) was added methyl isocyanate (0.26 ml) at ambient temperature, under nitrogen, with stirring for ten mins. Milled potassium carbonate was added and the reaction mixture was stirred for 4 hrs, and filtered through a pad of celite. The solids were washed with ethyl acetate, and the combined filtrates were concentrated. The residue was purified by flash column chromatography (silica gel, dichloromethane/0-30% methanol), and the eluant flushed through alumina (ethyl acetate) to give 1.0 g (96%) of product. Recrystallization from ether/petroleum ether gave the analytical sample, mp 67°-69° C.

Workup

  1. stirringthe reaction mixture was stirred for 4 hrs
  2. filtrationfiltered through a pad of celite
  3. washThe solids were washed with ethyl acetate
  4. concentrationthe combined filtrates were concentrated
  5. customThe residue was purified by flash column chromatography (silica gel, dichloromethane/0-30% methanol)
  6. customthe eluant flushed through alumina (ethyl acetate)

Sources & evidence

ORD record
ord-f0728ea329574373887cd3f568c0b62f
Source dataset
uspto-grants-1997_01
Patent number
US05591856

Reaction notes

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