Methylamine → HCID 24887103, compound

HRID 1435776Notes

Reaction equation

HRID 1435776 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C@H:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=O)[CH2:11]2)=[CH:2]1.[CH3:20][NH2:21].C(O[Si](OCC)(OCC)OCC)C.[H][H]>CO.O=[Pt]=O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C@H:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C@@H:12]([NH:21][CH3:20])[CH2:11]2)=[CH:2]1

Participants

7

Reactant 4

HCID 6329MethylamineHCID 6517TetraethoxysilaneHCID 68895059HCID 68895059, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 24887103HCID 24887103, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

(R)-3-(1H-indol-3-yl)-indan-1-one, methyl amine (5 mL 2M in THF) and 1 mL tetraethoxy silane in 10 mL methanol were stirred 11 minutes at 150° C. under microwave irradiation using the Emry Optimizer™ instrument. PtO2 (10 mg) was added and the reaction mixture was stirred under 1 atm. hydrogen over night at room temperature, filtered and concentrated in vacuo. [(1S,3R)-3-(1H-Indol-3-yl)-indan-1-yl]-methyl-amine was isolated in 66% yield after flash chromatography (ethyl acetate, methanol, triethylamine, silica gel).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c369709736e444e781c5db8d8882068e
Source dataset
uspto-grants-2009_11
Patent number
US07618967B2

Reaction notes

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