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

HRID 742604Notes

Reaction equation

HRID 742604 reaction equation
[C:1]1([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:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:20][N:21]=[C:22]=[O:23].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH3:20][NH:21][C:22](=[O:23])[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:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12228Methyl IsocyanateHCID 233612863-(1-Phenylmethyl-2-pyrrolidinyl)phenol

Product 1

HCID 233613173-[1-Phenylmethyl-2-pyrrolidinyl]phenyl methylcarbamateYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[1-phenylmethyl-2-pyrrolidinyl]phenol (1.0 g) in dry tetrahydrofuran (50 ml) was added methyl isocyanate (0.24 ml) followed by milled potassium carbonate (0.7 g) at ambient temperature, under nitrogen. The reaction mixture was stirred for 1 hr, filtered through a pad of celite, and the filter cake was washed with ethyl acetate. The combined filtrates were concentrated. The residue was purified by flash column chromatography (silica gel, dichloromethane/0-10% ethyl acetate). The appropriate fractions were collected and concentrated to give 0.8 g (70%) of product.

Workup

  1. filtrationfiltered through a pad of celite
  2. washthe filter cake was washed with ethyl acetate
  3. concentrationThe combined filtrates were concentrated
  4. customThe residue was purified by flash column chromatography (silica gel, dichloromethane/0-10% ethyl acetate)
  5. customThe appropriate fractions were collected
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4be71c85a0034b8787210a1ee274295a
Source dataset
uspto-grants-1996_09
Patent number
US05554750

Reaction notes

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