Triethylamine → HCID 58594484, compound

HRID 890342Notes

Reaction equation

HRID 890342 reaction equation
COC([N:5]1[CH:10]=[C:9]([C@@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2[CH3:16])[CH2:8][C:7]([CH:17]=[O:18])=[CH:6]1)=O.C(N(CC)CC)C>CO>[CH3:16][N:12]1[CH2:13][CH2:14][CH2:15][C@H:11]1[C:9]1[CH2:8][C:7]([CH:17]=[O:18])=[CH:6][NH:5][CH:10]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 11615761(S)-3-formyl-5-(1-methylpyrrolidin-2-yl)-4H-pyridine-1-carboxylic Acid Methyl Ester

Product 1

HCID 58594484HCID 58594484, compoundYield 104%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-3-formyl-5-(1-methyl-pyrrolidin-2-yl)-4H-pyridine-1-carboxylic acid methyl ester III (0.0124 g, 0.05 mmol) in 2 mL of anhydrous MeOH was slowly added triethylamine (0.02 mL, 0.15 mmol), and the reaction mixture was stirred at RT for 1 day. Evaporation of the solvent afforded a quantitative yield (0.010 g) of (S)-5-(1-methyl-pyrrolidin-2-yl)-1,4-dihydro-pyridine-3-carbaldehyde IV as a yellow oil. The product was used without further purification. IR (thin film, neat, NaCl): 3416–3244, 2957, 1595, 1509, 1377, 1228 cm−1. 1H NMR (CDCl3, 300 MHz) δ 9.14 (s, 1 H), 6.85 (d, 1 H, J=6 Hz), 6.48 (s, 1 H), 6.00–5.99 (m, 1 H), 3.05–3.00 (m, 3 H), 2.45 (m, 1 H), 2.19–2.11 (m, 4 H), 1.83–1.67 (m, 4 H); 13C NMR (CDCl3, 75 MHz) δ 189.59, 146.95, 119.91, 119.01, 112.67, 70.03, 57.03, 40.69, 28.96, 22.80, 20.37. HRMS Calcd for C11H16N2O: 193.1341 [M+H]+. Found: 193.1334 [M+H]+. [α]28D−80.7 (c=0.55, CH2Cl2).

Workup

  1. customEvaporation of the solvent

Sources & evidence

ORD record
ord-a9729781e3754987ab478b83b5852fb5
Source dataset
uspto-grants-2006_02
Patent number
US06995265B2

Reaction notes

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