Methanol → HCID 22481040, compound

HRID 412684Notes

Reaction equation

HRID 412684 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])=[C:40]([F:45])[CH:39]=3)[C:10]1=2)(C(C)(C)C)(C)C.CO.O1CCCC1>Cl>[CH:21]1([C:13]2[C:12]([CH:26]([F:37])[C:27]3[CH:28]=[CH:29][C:30]([C:33]([F:36])([F:34])[F:35])=[CH:31][CH:32]=3)=[C:11]([C:38]3[CH:43]=[CH:42][C:41]([F:44])=[C:40]([F:45])[CH:39]=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

5

Reactant 3

HCID 887MethanolHCID 8028TetrahydrofuranHCID 22481031HCID 22481031, compound

Product 1

HCID 22481040HCID 22481040, compoundYield 25.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

190 mg of 5-(tert-butyldimethylsilanyloxy)-2-cyclopentyl-4-(3,4-difluorophenyl)-3-[fluoro-(4-trifluoromethylphenyl)-methyl]-7,7dimethyl-5,6,7,8-tetra-hydroquinoline, in a mixture of 1.6 ml of 5 N hydrochloric acid, 2.3 ml of methanol and 1.5 ml of tetrahydrofuran, were stirred at RT for 1 hour and then at 40° C.-45° C. for 2 hours. Some of the compound precipitated out as a by-product. This gives 80 mg of m.p. 206-207° C. The mother liquor is admixed with saturated aqueous sodium bicarbonate solution and with ethyl acetate. The organic phase is once more washed with saturated aqueous sodium bicarbonate solution and then dried. The solvent is distilled off under reduced pressure and the residue is then purified over a silica gel column. Crystallization with heptane gives 40 mg of the base of m.p. 149-150° C.

Workup

  1. waitat 40° C.-45° C. for 2 hours
  2. customSome of the compound precipitated out as a by-product
  3. washThe organic phase is once more washed with saturated aqueous sodium bicarbonate solution
  4. customdried
  5. distillationThe solvent is distilled off under reduced pressure
  6. customthe residue is then purified over a silica gel column
  7. customCrystallization with heptane

Sources & evidence

ORD record
ord-b70b5ee7843345ddb359de1cd8ffcca0
Source dataset
uspto-grants-2003_05
Patent number
US06562976B2

Reaction notes

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