Potassium Hydroxide → HCID 58230579, compound

HRID 390405Notes

Reaction equation

HRID 390405 reaction equation
C([O:3][C:4](=[O:44])[CH2:5][CH2:6][C:7]1[CH:42]=[CH:41][C:10]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][N:20]3[CH2:25][CH2:24][C:23]4([C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[N:27]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:26]4)[CH2:22][CH2:21]3)=[CH:15][CH:14]=2)=[CH:9][C:8]=1[F:43])C.[OH-].[K+]>C(O)C.O>[C:37]([O:36][C:34]([N:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:23]2([CH2:22][CH2:21][N:20]([CH2:19][C:16]3[CH:15]=[CH:14][C:13]([CH2:12][O:11][C:10]4[CH:41]=[CH:42][C:7]([CH2:6][CH2:5][C:4]([OH:44])=[O:3])=[C:8]([F:43])[CH:9]=4)=[CH:18][CH:17]=3)[CH2:25][CH2:24]2)[CH2:26]1)=[O:35])([CH3:40])([CH3:38])[CH3:39]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 67087096HCID 67087096, compound

Product 1

HCID 58230579HCID 58230579, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of tert-butyl 1′-[[4-[[4-(3-ethoxy-3-oxo-propyl)-3-fluoro-phenoxy]methyl]phenyl]methyl]spiro[indoline-3,4′-piperidine]-1-carboxylate (0.32 g, 0.53 mmol) and KOH (0.148 g, 2.65 mmol) in ethanol:water (3:1, 4 mL) is stirred at room temperature for 16 hours. The reaction mixture is evaporated to dryness. The residue is re-dissolved in water (8 mL), cooled to 0° C., acidified with 1.5 N HCl to pH˜6, and extracted with EtOAc (3×15 mL). The combined organic layer is washed with water (15 mL) and saturated brine solution (15 mL), dried with a drying agent, filtered, and evaporated to dryness to give the title compound as an off-white solid (0.22 g, 72.1%). ESI/MS m/z 575.6 (M+H)+.

Workup

  1. customThe reaction mixture is evaporated to dryness
  2. dissolutionThe residue is re-dissolved in water (8 mL)
  3. temperaturecooled to 0° C.
  4. extractionextracted with EtOAc (3×15 mL)
  5. washThe combined organic layer is washed with water (15 mL) and saturated brine solution (15 mL)
  6. customdried with a drying agent
  7. filtrationfiltered
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-568855038cca48bb8fcd96140ac9b1a1
Source dataset
uspto-grants-2013_02
Patent number
US08383642B2

Reaction notes

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