Methanol → 1-{1-[2-(7-methoxy-2,2-dimethyl-4-oxochroman-8-yl)ethyl]piperidin-4-yl}-1H-indole-6-carboxylic acid

HRID 1640065Notes

Reaction equation

HRID 1640065 reaction equation
[CH3:1][O:2][C:3]1[C:12]([CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([N:21]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([C:30]([O:32]C)=[O:31])[CH:28]=4)[CH:23]=[CH:22]3)[CH2:17][CH2:16]2)=[C:11]2[C:6]([C:7](=[O:36])[CH2:8][C:9]([CH3:35])([CH3:34])[O:10]2)=[CH:5][CH:4]=1.[OH-].[Na+].CO>O1CCCC1>[CH3:1][O:2][C:3]1[C:12]([CH2:13][CH2:14][N:15]2[CH2:16][CH2:17][CH:18]([N:21]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([C:30]([OH:32])=[O:31])[CH:28]=4)[CH:23]=[CH:22]3)[CH2:19][CH2:20]2)=[C:11]2[C:6]([C:7](=[O:36])[CH2:8][C:9]([CH3:34])([CH3:35])[O:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 59439452methyl 1-{1-[2-(7-methoxy-2,2-dimethyl-4-oxochroman-8-yl)ethyl]piperidin-4-yl}-1H-indole-6-carboxylate

Product 1

HCID 594394671-{1-[2-(7-methoxy-2,2-dimethyl-4-oxochroman-8-yl)ethyl]piperidin-4-yl}-1H-indole-6-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

4.0 g of the above crude product of methyl 1-{1-[2-(7-methoxy-2,2-dimethyl-4-oxochroman-8-yl)ethyl]piperidin-4-yl}-1H-indole-6-carboxylate was dissolved in 40.0 mL of tetrahydrofuran and added with 16 mL of 1 N aqueous sodium hydroxide. 20 mL of methanol was added to remove the separation of layers of the reaction mixture, and the reaction mixture was stirred at 40° C. for about 20.5 hours. When the reaction mixture was cooled with an ice-water bath and the pH was adjusted to 7 with 15 mL of 1 N hydrochloric acid, crystals precipitated. 10 mL of water was further added to this slurry, and crystals were obtained by filtration and the crystals were washed with 24 mL of a mixture of 2-propanol and water (1:5). The crystals were dried in vacuo and 3.34 g of the title compound was obtained.

Workup

  1. customto remove
  2. customthe separation of layers of the reaction mixture
  3. temperatureWhen the reaction mixture was cooled with an ice-water bath
  4. customprecipitated
  5. addition10 mL of water was further added to this slurry
  6. customcrystals were obtained by filtration
  7. washthe crystals were washed with 24 mL of a mixture of 2-propanol and water (1:5)
  8. customThe crystals were dried in vacuo

Sources & evidence

ORD record
ord-c23743a2e1184a10981eda18d9a7b4c3
Source dataset
uspto-grants-2012_02
Patent number
US08110688B2

Reaction notes

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