Sodium sulfate decahydrate → HCID 59831705, compound

HRID 1716788Notes

Reaction equation

HRID 1716788 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O[C:12](=O)[NH:13][CH2:14][CH:15]([C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[NH:27][CH:26]=[CH:25]2)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(C)(C)C.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[NH:27]1[C:28]2[C:24](=[CH:23][C:22]([CH:15]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:14][NH:13][CH3:12])=[CH:30][CH:29]=2)[CH:25]=[CH:26]1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 67357680HCID 67357680, compound

Product 1

HCID 59831705HCID 59831705, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (54 mg, 1.4 mmol) was added, under nitrogen atmosphere, to a solution of [2-(1H-indol-5-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester CCLXXV (100 mg, 0.30 mmol) in tetrahydrofuran (3 mL) and the resulting mixture was heated at reflux for 95 minutes. The reaction mixture was cooled to room temperature and then at 0° C., freshly crushed sodium sulfate decahydrate (3 g) was then added portionwise and the resulting mixture was stirred for 1.5 hours. The reaction mixture was filtered and the filter cake was washed with ethyl acetate. The filtrate was evaporated under reduced pressure to a light yellow oil. This crude residue was purified by flash chromatography (DCM/(DCM/MeOH/NH4OH) 100/0 to 25/75) to give [2-(1H-indol-5-yl)-2-phenyl-ethyl]-methyl-amine CCLXXVI. MS=251 [M+H]+.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 95 minutes
  3. filtrationThe reaction mixture was filtered
  4. washthe filter cake was washed with ethyl acetate
  5. customThe filtrate was evaporated under reduced pressure to a light yellow oil
  6. customThis crude residue was purified by flash chromatography (DCM/(DCM/MeOH/NH4OH) 100/0 to 25/75)

Sources & evidence

ORD record
ord-5c66526c618a4b10818b239370c50a09
Source dataset
uspto-grants-2010_09
Patent number
US07803830B2

Reaction notes

Loading…