Formaldehyde → 2,3,4,9-Tetrahydro-1H-beta-carboline-3-carboxylic acid methyl ester

HRID 2369343

Reaction equation

HRID 2369343 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].[CH2:17]=O>CO>[CH2:17]1[C:8]2[NH:9][C:10]3[C:15]([C:7]=2[CH2:6][CH:4]([C:3]([O:2][CH3:1])=[O:16])[NH:5]1)=[CH:14][CH:13]=[CH:12][CH:11]=3

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 77980L-Tryptophan, methyl ester

Product 1

HCID 1777282,3,4,9-Tetrahydro-1H-beta-carboline-3-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of L-tryptophane methyl ester (25.4 g, 100 mmol) and 37% formaldehyde solution (12.5 mL) in aqueous methanol (170 mL; H2O:MeOH, v/v 10:1) was stirred at room temperature for 5 h. The reaction mixture was evaporated to dryness in vacuo. The residue was basified with sodium bicarbonate to give methyl 1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate, 14.4 g (63%); mp 161-162° C. (lit.19 mp 164-165° C.). 1H NMR (DMSO-d6) δ 2.78 (1H, m, CH2), 2.98 (1H, m, CH2), 3.66 (3H, s, COOMe), 3.85 (1H, m, CH), 4.02 (2H, q, J=15.8 Hz, NCH2), 6.92-6.96 (1H, m, ArH), 7.00-7.04 (1H, m, ArH), 7.27-7.29 (1H, m, ArH), 7.37-7.39 (1H, m, ArH), 10.78 (1H, s, exchangeable NH).

Workup

  1. customThe reaction mixture was evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-23431a8d9fb540638fcbc23204f84309
Source dataset
uspto-grants-2014_04
Patent number
US08703951B2

Linked notes

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