5-Methoxytryptamine → Tetrahydro-beta-carboline

HRID 2192236Notes

Reaction equation

HRID 2192236 reaction equation
CO[C:3]1[CH:14]=[C:13]2[C:6]([NH:7][CH:8]=[C:9]2[CH2:10][CH2:11][NH2:12])=[CH:5][CH:4]=1.[CH3:15]OC1C=C2C(=CC=1)C(CCN)=CN2.C(O)(C(F)(F)F)=O>C1COCC1>[CH2:15]1[C:8]2[NH:7][C:6]3[C:13](=[CH:14][CH:3]=[CH:4][CH:5]=3)[C:9]=2[CH2:10][CH2:11][NH:12]1

Participants

5

Reactant 3

HCID 18335-MethoxytryptamineHCID 6422Trifluoroacetic acidHCID 176542-(2-Aminoethyl)-5-methoxyindole

Product 1

HCID 107838Tetrahydro-beta-carboline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

5-Methoxy tryptamine 1a or 6-methoxy tryptamine 1b (0.524 mmol) and appropriate aryl or heteroaryl aldehyde 2 (0.63 mmol) were dissolved in THF (20 mL). The reaction mixture was cooled to 0° C. CF3COOH (0.2 ml) was then added at 0° C., and the reaction mixture was then allowed to stir at 0° C. for 1 hr. The ice bath was then removed and the reaction allowed to stir for a further 1 hr from 0° C. to r.t. The reaction mixture was quenched with aqueous saturated NaHCO3 (5 ml) and the organic phase separated. The mixture was extracted with EtOAc (2×10 ml). The combined organic phase was dried (anhydrous NaSO4), filtered and evaporated in vacuo to give the crude product tetrahydro β-carboline 3. The crude product was directly used for second step with out further purification.

Workup

  1. customThe ice bath was then removed
  2. stirringto stir for a further 1 hr from 0° C. to r.t
  3. customThe reaction mixture was quenched with aqueous saturated NaHCO3 (5 ml)
  4. customthe organic phase separated
  5. extractionThe mixture was extracted with EtOAc (2×10 ml)
  6. dry with materialThe combined organic phase was dried (anhydrous NaSO4)
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-d9603516494544ef85987c73bf5cd023
Source dataset
uspto-grants-2012_12
Patent number
US08329723B2

Reaction notes

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