Water → HCID 45264916, compound

HRID 1460664Notes

Reaction equation

HRID 1460664 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][O:14][CH:15]=[C:16]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=2[CH3:32])[C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=2[CH3:24])[CH2:7]1)=[O:5])C.[OH-].[Na+].O.[Cl:36][Si](C)(C)C>C(O)C.C1(C)C=CC=CC=1.CO>[ClH:36].[F:31][C:28]1[CH:29]=[CH:30][C:25]([C:16]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=2[CH3:24])=[CH:15][O:14][CH2:13][CH2:12][N:8]2[CH2:9][CH2:10][CH2:11][C@@H:6]([C:4]([OH:5])=[O:3])[CH2:7]2)=[C:26]([CH3:32])[CH:27]=1

Participants

8

Reactant 4

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 14798Sodium HydroxideHCID 10528708HCID 10528708, compound

Product 1

HCID 45264916HCID 45264916, compoundYield 44%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

(R)-1-[2-[[2,2-bis(4-Fluoro-2-methylphenyl)ethenyl]oxy]ethyl]-3-piperidine carboxylic acid ethyl ester (1.72 g, 0.0039 mol) (prepared as described in Method D) was dissolved in ethanol (20 ml) and 10N sodium hydroxide solution (4 ml) was introduced. The solution was stirred at room temperature for 3 h and water (100 ml) was added. The solution was extracted with diethyl ether (2×100 ml) and the aqueous phase was acidified to pH 5 with 2N hydrochloric acid solution. Extraction with dichloromethane (4×80 ml) and drying of the combined extracts (MgSO4) followed by evaporation gave a residue, which was dissolved in toluene (50 ml). Methanol (0.16 ml) and chlorotrimethylsilane (0.51 ml) were added, and the product precipitated. The mixture was evaporated to a solid and recrystallized from toluene to give the title compound as a white crystalline solid (0.78 g, 44%), m.p. 175°-185° (decomp.)

Workup

  1. extractionThe solution was extracted with diethyl ether (2×100 ml)
  2. extractionExtraction with dichloromethane (4×80 ml)
  3. dry with materialdrying of the combined extracts (MgSO4)
  4. customfollowed by evaporation
  5. customgave a residue, which
  6. customthe product precipitated
  7. customThe mixture was evaporated to a solid
  8. customrecrystallized from toluene

Sources & evidence

ORD record
ord-2200ca99554b408081ae2bbd111831d3
Source dataset
uspto-grants-1991_12
Patent number
US05071859

Reaction notes

Loading…