Hydrochloric Acid → HCID 67584014, compound

HRID 1456554Notes

Reaction equation

HRID 1456554 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][CH2:7][CH2:8][C@@H:9]2[CH2:13][C@@H:12]([OH:14])[CH2:11][N:10]2[CH3:15])=[C:4]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[C:22]([O:27][CH3:28])[CH:21]=2)[CH:3]=1.[ClH:29]>C(OCC)(=O)C>[ClH:29].[F:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][CH2:7][CH2:8][C@@H:9]2[CH2:13][C@@H:12]([OH:14])[CH2:11][N:10]2[CH3:15])=[C:4]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[C:22]([O:27][CH3:28])[CH:21]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67583627HCID 67583627, compound

Product 1

HCID 67584014HCID 67584014, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

399 mg of the (2R,4R)-2-[2-{4-fluoro-2-[2-(4-fluoro-3-methoxyphenyl)ethyl]phenoxy}ethyl]-4-hydroxy-1-methylpyrrolidine [prepared as described in step (b) above] were dissolved in 5 ml of ethyl acetate. Addition of 0.38 ml of a 4N solution of hydrogen chloride in ethyl acetate resulted in the precipitation of crystals. The solvent was removed by evaporation under reduced pressure, and the resulting solid substance was dissolved in a small quantity (approximately 0.5 ml) of methylene chloride and then 5 ml of ethyl acetate were added to the resulting solution. The resulting mixture was then allowed to stand at room temperature for about 10 minutes. The crystals which precipitated were collected by filtration, and dried in vacuo, to give 359 mg (yield 82%) of the title compound as colorless crystals, melting at 128-130° C.

Workup

  1. customresulted in the precipitation of crystals
  2. customThe solvent was removed by evaporation under reduced pressure
  3. dissolutionthe resulting solid substance was dissolved in a small quantity (approximately 0.5 ml) of methylene chloride
  4. addition5 ml of ethyl acetate were added to the resulting solution
  5. customThe crystals which precipitated
  6. filtrationwere collected by filtration
  7. customdried in vacuo

Sources & evidence

ORD record
ord-fad8d92633f3496ab6db301bfe0bdfb7
Source dataset
uspto-grants-1998_12
Patent number
US05843983

Reaction notes

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