Sodium sulfate decahydrate → HCID 59831705, compound

HRID 268906Notes

Reaction equation

HRID 268906 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-701a5e56ee66495db3d7b8034afe9f9b
Source dataset
uspto-grants-2008_11
Patent number
US07446118B2

Reaction notes

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