Methanol → HCID 59494238, compound

HRID 872043Notes

Reaction equation

HRID 872043 reaction equation
O1CCCC1.B.[CH:7]1([NH:10][CH2:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[N:17]([CH3:21])[CH:16]=[C:15]3[C:22](=O)[CH2:23][CH2:24][O:25][CH3:26])[CH2:9][CH2:8]1.[OH-].[Na+].CO>O1CCCC1>[CH3:26][O:25][CH2:24][CH2:23][CH2:22][C:15]1[C:14]2[C:18](=[CH:19][CH:20]=[C:12]([CH2:11][NH:10][CH:7]3[CH2:8][CH2:9]3)[CH:13]=2)[N:17]([CH3:21])[CH:16]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 67542209HCID 67542209, compound

Product 1

HCID 59494238HCID 59494238, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1M tetrahydrofuran-solution of borane tetrahydrofuran (2.62 ml) was added dropwise to a solution of 1-{5-[(cyclopropylamino)methyl]-1-methyl-1H-indol-3-yl}-3-methoxy propan-1-one (150 mg) in tetrahydrofuran (2.5 ml) under ice-cooling and the mixture was stirred at room temperature for 15 hours. A 5N aqueous solution of sodium hydroxide (2.5 ml) and methanol (1.25 ml) were added to the reaction mixture and it was stirred at 50° C. for 24 hours. The reaction mixture was cooled to room temperature, extracted with diethyl ether. The organic layer was washed with saturated brine, dried over sodium sulfate and concentrated in vacuo. The resulted residue was purified with a silica gel column chromatography (eluting solvent: chloroform to chloroform/methanol=5/1) to give N-{[3-(3-methoxypropyl)-1-methyl-1H-indol-5-yl]methyl}cyclopropanamine (107 mg) as a colorless oil.

Workup

  1. temperaturecooling
  2. stirringwas stirred at 50° C. for 24 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. extractionextracted with diethyl ether
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe resulted residue was purified with a silica gel column chromatography (eluting solvent: chloroform to chloroform/methanol=5/1)

Sources & evidence

ORD record
ord-919d1e2a30fb4dda84c49fbd6b7283a2
Source dataset
uspto-grants-2015_03
Patent number
US08975252B2

Reaction notes

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