Water → HCID 68890021, compound

HRID 1760609Notes

Reaction equation

HRID 1760609 reaction equation
C[SiH](C)[O:3][CH:4](C(C)(C)C(C)C)[C@H:5]1[N:10]2[C:11]3[CH:12]=[C:13]([C:18]([F:21])([F:20])[F:19])[CH:14]=[CH:15][C:16]=3[CH:17]=[C:9]2[C:8](=O)[NH:7][CH2:6]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.O>C1COCC1>[NH3:7].[F:21][C:18]([F:19])([F:20])[C:13]1[CH:14]=[CH:15][C:16]2[CH:17]=[C:9]3[CH2:8][NH:7][CH2:6][C@@H:5]([CH2:4][OH:3])[N:10]3[C:11]=2[CH:12]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 137331190HCID 137331190, compound

Product 2

HCID 222AmmoniaYield 25%HCID 68890021HCID 68890021, compoundYield 144.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 0.240 g (S)-4-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-7-trifluoromethyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one in 3 ml THF was added 1.2 ml of a 1M solution of lithium aluminium hydride in THF. The mixture was heated to reflux for 1 h. The reaction mixture was cooled to room temperature and the 10 ml ethyl acetate and 10 ml water were added. The phases were separated and the organic phase was purified by chromatography on silica gel with 190:10:1 dichloromethane:methanol:25% aqueous ammonia eluant to yield 0.11 g of the title compound as white crystals (m.p.: 126-127° C.).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 h
  3. customThe phases were separated
  4. customthe organic phase was purified by chromatography on silica gel with 190:10:1 dichloromethane

Sources & evidence

ORD record
ord-2e3d6e198f9e4522a24c893e6a4297bc
Source dataset
uspto-grants-2005_01
Patent number
US06844345B2

Reaction notes

Loading…