Water → HCID 68890297, compound

HRID 853047Notes

Reaction equation

HRID 853047 reaction equation
[CH3:1][C@H:2]1[N:7]2[C:8]3[CH:9]=[C:10]([C:15]([F:18])([F:17])[F:16])[CH:11]=[CH:12][C:13]=3[CH:14]=[C:6]2[C:5](=O)[NH:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C(OCC)C>[CH3:1][C@H:2]1[N:7]2[C:8]3[CH:9]=[C:10]([C:15]([F:17])([F:16])[F:18])[CH:11]=[CH:12][C:13]=3[CH:14]=[C:6]2[CH2:5][NH:4][CH2:3]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 68889281HCID 68889281, compound

Product 1

HCID 68890297HCID 68890297, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

(R)-4-Methyl-7-trifluoromethyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one (2.75 g; 10 mmol) was dissolved in diethylether (200 mL) and lithium aluminium hydride (0.78 g, 21 mmol) was added in portions with cooling. The solution was stirred for 2 h at reflux temperature, cooled and hydrolyzed by sequential addition of water (3.0 mL), sodium hydroxide solution (15%, 6.0 mL) and water (6.0 mL). Diethylether was added (100 mL), the mixture was filtered and the filtrate evaporated. The residue was stirred with hexane (20 mL) and diethylether (1 mL) to give the title compound as white solid (2.55 g, 97%). M.p.: 123–125° C., ISP-MS: m/e=255.1 (M+), αD20=−110.0

Workup

  1. temperaturewith cooling
  2. temperatureat reflux temperature
  3. filtrationthe mixture was filtered
  4. customthe filtrate evaporated
  5. stirringThe residue was stirred with hexane (20 mL) and diethylether (1 mL)

Sources & evidence

ORD record
ord-10116726bf3b4ef282110fba882217c8
Source dataset
uspto-grants-2007_08
Patent number
US07253281B2

Reaction notes

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