Potassium Carbonate → 3-[1-(4-Pyridinylmethyl)-2-pyrrolidinyl]phenyl methylcarbamate

HRID 742562Notes

Reaction equation

HRID 742562 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[CH2:12][CH2:11][CH2:10][CH:9]2[C:13]2[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=2)=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:26][N:27]=[C:28]=[O:29]>O1CCCC1>[CH3:26][NH:27][C:28](=[O:29])[O:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([CH:9]2[CH2:10][CH2:11][CH2:12][N:8]2[CH2:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[CH:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12228Methyl IsocyanateHCID 152932263-[1-(4-Pyridinylmethyl)-2-pyrrolidinyl]phenol

Product 1

HCID 99048253-[1-(4-Pyridinylmethyl)-2-pyrrolidinyl]phenyl methylcarbamateYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-[1-(4-pyridinylmethyl)-2-pyrrolidinyl]phenol (0.60 g) in dry tetrahydrofuran (16 ml) was added milled potassium carbonate (0.36 g), followed by methyl isocyanate (0.15 ml), dropwise, at ambient temperature, under nitrogen, with stirring. The mixture was stirred for 17 hrs and filtered through a pad of celite. The filter cake was washed with ethyl acetate, and the filtrate was concentrated. The residue was purified by flash column chromatography (silica gel, ether). The appropriate fractions were collected and concentrated to afford 0.63 g (86%) of product. Trituration of the residue with petroleum ether gave the analytical sample, mp 92°-105° C.

Workup

  1. stirringThe mixture was stirred for 17 hrs
  2. filtrationfiltered through a pad of celite
  3. washThe filter cake was washed with ethyl acetate
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by flash column chromatography (silica gel, ether)
  6. customThe appropriate fractions were collected
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4c7a7ec30c4b4ad188c6d4d9d86ec562
Source dataset
uspto-grants-1996_09
Patent number
US05554750

Reaction notes

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