4-Hydroxybenzaldehyde → Methyl 1,2,3,4-tetrahydro-1-(4-hydroxyphenyl)-9h-pyrido(3,4-b)indole-3-carboxylate

HRID 611510Notes

Reaction equation

HRID 611510 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C@H:4]([CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)[NH2:5].[OH:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1.FC(F)(F)C(O)=O>ClCCl>[OH:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]2[C:8]3[NH:9][C:10]4[C:15]([C:7]=3[CH2:6][CH:4]([C:3]([O:2][CH3:1])=[O:16])[NH:5]2)=[CH:14][CH:13]=[CH:12][CH:11]=4)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 6422Trifluoroacetic acidHCID 77980L-Tryptophan, methyl ester

Product 1

HCID 11186332Methyl 1,2,3,4-tetrahydro-1-(4-hydroxyphenyl)-9h-pyrido(3,4-b)indole-3-carboxylateYield 78.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of racemic tryptophan methyl ester (3 g ) and 4-hydroxybenzaldehyde (1.84 g) in anhydrous dichloromethane (50 mL) cooled at 0° C. was added dropwise trifluoroacetic acid (1.27 mL) and the solution was allowed to react at ambient temperature. After 22 hours, the solution was washed with a saturated solution of NaHCO3, then with water, dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography eluting with ethyl acetate to give the title compound (3.48 g) as an off-white solid m.p.:233-235° C.

Workup

  1. customto react at ambient temperature
  2. washthe solution was washed with a saturated solution of NaHCO3
  3. dry with materialwith water, dried over Na2SO4
  4. customevaporated to dryness
  5. customThe residue was purified by flash chromatography
  6. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-5115323179ef42c0b744a99fae42ee37
Source dataset
uspto-grants-1999_12
Patent number
US06001847

Reaction notes

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