Tryptophol → N-[1-(1,3,4,9-Tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)ethyl]acetamide

HRID 647587Notes

Reaction equation

HRID 647587 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][OH:12])=[CH:2]1.[CH3:13][CH:14]([NH:18][C:19](=[O:21])[CH3:20])[C:15](=O)[CH3:16]>B(F)(F)F.CCOCC.C1C=CC=CC=1>[CH3:16][C:15]1([CH:14]([NH:18][C:19](=[O:21])[CH3:20])[CH3:13])[C:2]2[NH:1][C:9]3[C:4]([C:3]=2[CH2:10][CH2:11][O:12]1)=[CH:5][CH:6]=[CH:7][CH:8]=3

Participants

5

Reactant 2

HCID 10685TryptopholHCID 97923N-(1-methyl-2-oxopropyl)acetamide

Product 1

HCID 12708188N-[1-(1,3,4,9-Tetrahydro-1-methylpyrano[3,4-b]indol-1-yl)ethyl]acetamide

Reagents, catalysts & solvents 2

HCID 8000Boron trifluoride etherateCatalystHCID 241BenzeneSolvent

Procedure

A mixture of indole-3-ethanol (16.1 g), benzene (1200 ml), N-(1-methyl-2-oxopropyl)-acetamide[12.7 g, described by A. Triebs and W. Sutter, Chem. Ber. 84, 96(1951)] and boron trifluoride-etherate (5 drops) is refluxed using a water separating condenser for 60 minutes. After cooling, the mixture is washed with concentrated sodium bicarbonate, dried over magnesium sulfate and evaporated. The residue is chromatographed on silica gel using chloroform. The eluates are evaporated to give a residue of the title compound as a 1:1 mixture of diastereoisomers:

Workup

  1. customfor 60 minutes
  2. temperatureAfter cooling
  3. washthe mixture is washed with concentrated sodium bicarbonate
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue is chromatographed on silica gel
  7. customThe eluates are evaporated

Sources & evidence

ORD record
ord-95788004af7e4f22990074913ccd93f3
Source dataset
uspto-grants-1983_10
Patent number
US04409224

Reaction notes

Loading…