7-(Methoxymethoxy)-3-(4-methoxymethoxyphenyl)-4-{9-[4-(4,4,5,5,5-pentafluoropentyl)piperazinyl]nonyl}-3-methylchroman → 7-Hydroxy-3-(4-hydroxyphenyl)-3-methyl-4-{9-[4-(4,4,5,5,5-pentafluoropentyl)piperazinyl]nonyl}chroman

HRID 1792291Notes

Reaction equation

HRID 1792291 reaction equation
COC[O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][N:35]3[CH2:40][CH2:39][N:38]([CH2:41][CH2:42][CH2:43][C:44]([F:50])([F:49])[C:45]([F:48])([F:47])[F:46])[CH2:37][CH2:36]3)[C:10]([C:16]3[CH:21]=[CH:20][C:19]([O:22]COC)=[CH:18][CH:17]=3)([CH3:15])[CH2:11][O:12]2)=[CH:7][CH:6]=1>Cl.CO>[OH:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][N:35]3[CH2:40][CH2:39][N:38]([CH2:41][CH2:42][CH2:43][C:44]([F:50])([F:49])[C:45]([F:48])([F:46])[F:47])[CH2:37][CH2:36]3)[C:10]([C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=3)([CH3:15])[CH2:11][O:12]2)=[CH:7][CH:6]=1

Participants

4

Reactant 1

HCID 220332377-(Methoxymethoxy)-3-(4-methoxymethoxyphenyl)-4-{9-[4-(4,4,5,5,5-pentafluoropentyl)piperazinyl]nonyl}-3-methylchroman

Product 1

HCID 99171957-Hydroxy-3-(4-hydroxyphenyl)-3-methyl-4-{9-[4-(4,4,5,5,5-pentafluoropentyl)piperazinyl]nonyl}chromanYield 88%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

7-(Methoxymethoxy)-3-(4-methoxymethoxyphenyl)-4-{9-[4-(4,4,5,5,5-pentafluoropentyl)piperazinyl]nonyl}-3-methylchroman (210 mg, 0.294 mmol) was dissolved in 2N-HCl solution in methanol, and the mixture was stirred at 50° C. for 1 hour. The mixture was cooled down to room temperature, adjusted to pH=9 using aqueous NaHCO solution, and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the organic solvent was removed under reduced pressure. The concentrate was subjected to column chromatography (n-hexane:ethyl acetate=1:1) to give 162 mg (yield: 88%. (3RS,4RS):(3RS,4SR)=8:5) of the title compound as a white solid.

Workup

  1. temperatureThe mixture was cooled down to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe organic solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-502f9fd81a9f4c6b8b752215ee2a5228
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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