(2R)-1-(1H-Indol-3-YL)propan-2-amine → (R)-alpha-[[(1(R)-methyl-2-(1H-indol-3-yl)ethyl)amino]-methyl]tetrazolo[1,5-a]pyridine-6-methanol

HRID 1086479Notes

Reaction equation

HRID 1086479 reaction equation
[N:1]1[N:2]=[N:3][N:4]2[CH:9]=[C:8]([C@@H:10]3[CH2:12][O:11]3)[CH:7]=[CH:6][C:5]=12.[CH3:13][C@H:14]([CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1)[NH2:15]>C(O)C>[CH3:13][C@@H:14]([NH:15][CH2:12][C@@H:10]([C:8]1[CH:7]=[CH:6][C:5]2[N:4]([N:3]=[N:2][N:1]=2)[CH:9]=1)[OH:11])[CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19][CH:18]=1

Participants

4

Reactant 2

HCID 448779(2R)-1-(1H-Indol-3-YL)propan-2-amineHCID 13090314(R)-2-(tetrazolo[1,5-a]pyrid 6-yl)oxirane

Product 1

HCID 15137721(R)-alpha-[[(1(R)-methyl-2-(1H-indol-3-yl)ethyl)amino]-methyl]tetrazolo[1,5-a]pyridine-6-methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 325 mg of (R)-2-(tetrazolo[1,5-a]pyrid-6-yl)oxirane and 300 mg of (R)-α-methyltryptamine in 6 ml of absolute ethanol is heated at reflux under nitrogen for two hours. The reaction mixture is concentrated and the residue purified by silica gel chromatography to give (R)-α-[[(1(R)-methyl-2-(1H-indol-3-yl)ethyl)amino]-methyl]tetrazolo[1,5-a]pyridine-6-methanol.

Workup

  1. temperatureat reflux under nitrogen for two hours
  2. concentrationThe reaction mixture is concentrated
  3. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-f8ba0c5e0293460a9c72056474a992c1
Source dataset
uspto-grants-1991_07
Patent number
US05030640

Reaction notes

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