Methanol → HCID 10118593, compound

HRID 1532981Notes

Reaction equation

HRID 1532981 reaction equation
[Si]([O:8][CH:9]1[CH2:18][C:17]([CH3:20])([CH3:19])[CH2:16][C:15]2[N:14]=[C:13]([CH:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)[C:12]([CH:26]([F:37])[C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=3)=[C:11]([C:38]3[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=3)[C:10]1=2)(C(C)(C)C)(C)C.CO.O1CCCC1.C(=O)([O-])O.[Na+]>Cl.C(OCC)(=O)C>[CH:21]1([C:13]2[C:12]([CH:26]([F:37])[C:27]3[CH:32]=[CH:31][C:30]([C:33]([F:35])([F:36])[F:34])=[CH:29][CH:28]=3)=[C:11]([C:38]3[CH:39]=[CH:40][C:41]([F:44])=[CH:42][CH:43]=3)[C:10]3[CH:9]([OH:8])[CH2:18][C:17]([CH3:20])([CH3:19])[CH2:16][C:15]=3[N:14]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 10282769HCID 10282769, compound

Product 1

HCID 10118593HCID 10118593, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

110 g of 5-(tert-butyldimethylsilanyloxy)-2-cyclopentyl-4-(4-fluorophenyl)-3-[fluoro-(4-trifluoromethylphenyl)-methyl]-7,7-dimethyl-5,6,7,8-tetrahydroquinoline were stirred at 40° C. for 2 hours in a mixture of 913 ml of 5 N hydrochloric acid, 1364 ml of methanol and 902 ml of tetrahydrofuran. Working up was carried out by pouring into saturated aqueous sodium hydrogencarbonate solution and extraction with ethyl acetate. The organic phases were dried after fresh washing with saturated aqueous sodium hydrogencarbonate solution. After distilling off the solvent in vacuo, the residue was recrystallized from cyclohexane. After drying in an oil-pump vacuum, a total of 71.1 g of colorless crystals having a purity of 99.4% according to HPLC (e.e. 99.5%) resulted. By chromatography on silica gel, it was possible from the mother liquor of the crystallization, using petroleum ether/ethyl acetate 7:1, to obtain a further 10.8 g of the same quality.

Workup

  1. customThe organic phases were dried
  2. washafter fresh washing with saturated aqueous sodium hydrogencarbonate solution
  3. distillationAfter distilling off the solvent in vacuo
  4. customthe residue was recrystallized from cyclohexane
  5. customAfter drying in an oil-pump vacuum
  6. customresulted
  7. customBy chromatography on silica gel, it was possible from the mother liquor of the crystallization
  8. customto obtain a further 10.8 g of the same quality

Sources & evidence

ORD record
ord-21f77e24ad2446edad032065701d7617
Source dataset
uspto-grants-2001_03
Patent number
US06207671B1

Reaction notes

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