Potassium Hydroxide → HCID 67430848, compound

HRID 454995Notes

Reaction equation

HRID 454995 reaction equation
Cl.Cl.[NH2:3][C@H:4]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C@@H:22]([CH3:25])[CH2:23][CH3:24])=[CH:16][CH:15]=1)[C:5]([N:7]1[CH2:12][CH2:11][N:10]([CH3:13])[CH2:9][CH2:8]1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[K+]>C1COCC1>[CH3:25][C@@H:22]([CH2:23][CH3:24])[CH2:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C@@H:4]([NH2:3])[CH2:5][N:7]2[CH2:8][CH2:9][N:10]([CH3:13])[CH2:11][CH2:12]2)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 21226445Aluminium lithium hydrideHCID 131730728HCID 131730728, compound

Product 1

HCID 67430848HCID 67430848, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To 200 mg (0.49 mmol) of (R)-2-Amino-2-[4-((S)-2-methyl-butoxy)-phenyl]-1-(4-methyl-piperazin-1-yl)-ethanone di-HCl salt in 10 mL of THF was added 5.9 mL LAH (1.0 M solution, 4.9 mmol). The resulting mixture was refluxed overnight. On the next day it was cooled to 0° C. and 0.5 mL of concentrated aq. KOH was slowly added. The ice bath was removed, and allowed it to stir for 1 hr, and then diluted with EtOAc, dried over MgSO4, filter and concentrated to obtain 68 mg (44%) of the product. The product obtained was pure enough to be used for the next step without further purification.

Workup

  1. temperatureThe resulting mixture was refluxed overnight
  2. customThe ice bath was removed
  3. additiondiluted with EtOAc
  4. dry with materialdried over MgSO4
  5. filtrationfilter
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3fd8eb0213244c3a9355863e89f1b7d5
Source dataset
uspto-grants-2013_07
Patent number
US08497271B2

Reaction notes

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