Potassium Carbonate → HCID 22293477, compound

HRID 966988Notes

Reaction equation

HRID 966988 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:10][CH:11]([C:28]1([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:37][CH2:36][C:31]2([O:35][CH2:34][CH2:33][O:32]2)[CH2:30][CH2:29]1)[CH2:12][CH2:13][C:14]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[C:16]([C:24]([F:27])([F:26])[F:25])[CH:15]=1)(=O)C>CO.O>[C:38]1([C:28]2([CH:11]([OH:10])[CH2:12][CH2:13][C:14]3[CH:19]=[C:18]([C:20]([F:21])([F:22])[F:23])[CH:17]=[C:16]([C:24]([F:27])([F:25])[F:26])[CH:15]=3)[CH2:37][CH2:36][C:31]3([O:35][CH2:34][CH2:33][O:32]3)[CH2:30][CH2:29]2)[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 22293532HCID 22293532, compound

Product 1

HCID 22293477HCID 22293477, compoundYield 88.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Potassium carbonate (1.75 g, 12.7 mmol) was added to a solution of (RS)-1-(8-phenyl-1,4-dioxaspiro[4.5]decan-8-yl)-3-[3,5-bis(trifluoromethyl)phenyl]propan-1-yl ethanoate (Example 23, 410 mg, 0.773 mmol) in methanol (15 mL) and water (2 mL) and the mixture was stirred at room temperature for 48 hours, then at 50° C. for 24 hours. The mixture was cooled and the methanol was evaporated under reduced pressure. Water (50 mL) was added and the mixture was extracted with ethyl acetate (2×50 mL). The combined organic fractions were dried (Na2SO4) and the solvent was evaporated under reduced pressure to give the title compound (334 mg, 88%). 1H NMR (400 MHz, CDCl3) δ 7.68 (1H, s), 7.53 (2H, s), 7.4-7.3 (4H, m), 7.3-7.2 (1H, m), 3.95-3.8 (4H, m), 3.36 (1H, br d, J 9 Hz), 2.91 (1H, ddd, J 14, 10, 5 Hz), 2.64 (1H, ddd, J 16, 9, 7.5 Hz), 2.5-2.4 (1H, m), 2.3-2.2 (1H, m), 1.9-1.7 (3H, m) and 1.65-1.20 (6H, m).

Workup

  1. waitat 50° C. for 24 hours
  2. temperatureThe mixture was cooled
  3. customthe methanol was evaporated under reduced pressure
  4. additionWater (50 mL) was added
  5. extractionthe mixture was extracted with ethyl acetate (2×50 mL)
  6. dry with materialThe combined organic fractions were dried (Na2SO4)
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f4dd7bf44249456889e19cb907851774
Source dataset
uspto-grants-2005_10
Patent number
US06953792B2

Reaction notes

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