Potassium Carbonate → 2-Oxodarifenacin

HRID 2253913Notes

Reaction equation

HRID 2253913 reaction equation
[Cl:1][CH2:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][CH2:11][CH2:10][C:9]=2[CH:13]=1)=[O:4].[C:14]([C:17]([C@@H:30]1[CH2:34][CH2:33][NH:32][CH2:31]1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:16])[NH2:15].C(=O)([O-])[O-].[K+].[K+]>>[ClH:1].[C:14]([C:17]([C@@H:30]1[CH2:34][CH2:33][N:32]([CH2:2][C:3]([C:5]2[CH:6]=[CH:7][C:8]3[O:12][CH2:11][CH2:10][C:9]=3[CH:13]=2)=[O:4])[CH2:31]1)([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:16])[NH2:15]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 65041702-Chloro-1-(2,3-dihydrobenzofuran-5-yl)ethanoneHCID 13633758(S)-2,2-Diphenyl-2-(pyrrolidin-3-yl)acetamide

Product 1

HCID 228428282-Oxodarifenacin

Procedure

A mixture of 5-chloroacetyl-2,3-dihydrobenzofuran (176.2 g-see Preparation 18), 3-(S)-(-)-(1-carbamoyl-1,1-diphenylmethyl)pyrrolidine (335.0 g-see Preparation 10(B)) and potassium carbonate (335 g) were stirred in industrial methylated spirits at room temperature for 18 hours then concentrated in vacuo. The oily solid was partitioned between methylene chloride (2,500 ml) and water (2,500 ml) and the organic phase was concentrated to an oil in vacuo. The oil was dissolved in ethyl acetate (3,350 ml) and acidified with hydrochloric acid dissolved in isopropyl alcohol (180.6 ml at 24% w/v). Filtration produced the title compound as a hygroscopic solid, yield 467 g.

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe oily solid was partitioned between methylene chloride (2,500 ml) and water (2,500 ml)
  3. concentrationthe organic phase was concentrated to an oil in vacuo
  4. dissolutionThe oil was dissolved in ethyl acetate (3,350 ml)
  5. dissolutiondissolved in isopropyl alcohol (180.6 ml at 24% w/v)
  6. filtrationFiltration

Sources & evidence

ORD record
ord-79ce3bba6874415a9526fe171e9b846d
Source dataset
uspto-grants-1993_08
Patent number
US05233053

Reaction notes

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