Ethanol → Ethyl 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-carboxylate

HRID 1723793Notes

Reaction equation

HRID 1723793 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1.CCO.[C:17]([O:21][CH2:22][CH3:23])(=[O:20])[CH:18]=O.N#N>C1(C)C=CC=CC=1>[CH2:22]([O:21][C:17]([CH:18]1[C:6]2[NH:7][C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:5]=2[CH2:4][CH2:3][NH:2]1)=[O:20])[CH3:23]

Participants

6

Reactant 4

HCID 702EthanolHCID 947NitrogenHCID 67652Tryptamine hydrochlorideHCID 70211Ethyl oxoacetate

Product 1

HCID 372325Ethyl 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-carboxylateYield 68%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,3,4,9-Tetrahydro-1H-betacarboline-1-carboxylic acid ethyl ester was prepared by the addition of tryptamine-HCl (1.33 g, 6.76 mmol), EtOH (12 mL), and a 50% toluene solution of ethyl glyoxylate (1.66 g, 8.11 mmol) to a 50 mL flask purged with N2. The reaction solution was allowed to reflux 16 hours. The reaction solution was concentrated under reduced pressure, and the resulting crude material was chromatographed (SiO2, 100% DCM to 4% MeOH) to provide 1.10 g (68% yield) of 2,3,4,9-tetrahydro-1H-betacarboline-1-carboxylic acid ethyl ester; 1H NMR (CDCl3) δ 8.59 (1H, br s), 7.46 (1H, d), 7.39 (1H, d), 7.23 (1H, t), 7.14 (1H, t), 5.40 (1H, s), 4.24 (2H, q), 3.51 (1H, m), 3.07 (1H, m), 2.86 (1H, d), 1.30 (3H, t); 13C NMR (CDCl3) 6166, 137, 126, 123, 122, 120, 119, 112, 108, 64, 60, 53, 41, 14; MS(ESI): 245 (MH+).

Workup

  1. temperatureto reflux 16 hours
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. customthe resulting crude material was chromatographed (SiO2, 100% DCM to 4% MeOH)

Sources & evidence

ORD record
ord-85b2353349014e96997abe090d232848
Source dataset
uspto-grants-2009_02
Patent number
US07485634B2

Reaction notes

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