Diisopropylethylamine → HCID 54244036, compound

HRID 2416685Notes

Reaction equation

HRID 2416685 reaction equation
[C:1]([CH:5]([CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:13]=1[CH2:20][NH:21][CH3:22])[CH2:6][C:7]([O:9][CH3:10])=[O:8])(OC)=[O:2].C(N(C(C)C)CC)(C)C>C1(C)C=CC=CC=1>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]2[CH2:11][CH:5]([CH2:6][C:7]([O:9][CH3:10])=[O:8])[C:1](=[O:2])[N:21]([CH3:22])[CH2:20][C:13]=2[CH:14]=1

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 54233162HCID 54233162, compound

Product 1

HCID 54244036HCID 54244036, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of methyl (±)-3-carbomethoxy-4-[2-(methylamino)methyl-4-methoxyphenyl]butanoate (11.06 mmole) and diisopropylethylamine (5.8 mL, 33.18 mmole) in toluene (110 mL) was heated at reflux for 25 hr, stirred at RT for 4 days, then heated at reflux for another 24 hr. Concentration and silica gel chromatography (5% MeOH in 1:1 EtOAc/CHCl3) gave the title compound (2.88 g, 94%) as a light yellow solid: TLC (5% MeOH in 1:1 EtOAc/CHCl3) Rf 0.63; 1H NMR (250, CDCl3) δ 7.02 (d, J=8.4 Hz, 1 H, 6.78 (dd, J=8.4, 2.7 Hz, 1 H), 6.63 (d, J=2.7 Hz, 1 H), 5.29 (d, J=16.3 Hz, 1 H), 3.50-3.90 (m, 2 H), 3.79 (s, 3 H), 3.71 (s, 3 H), 2.73-3.16 (m, 3 H), 3.04 (s, 3 H), 2.41 (dd, J=16.7, 5.4 Hz, 1 H; MS (ES) m/e 300 (M+Na)+, 278 (M+H)+.

Workup

  1. temperatureat reflux for 25 hr
  2. temperatureheated
  3. temperatureat reflux for another 24 hr
  4. concentrationConcentration and silica gel chromatography (5% MeOH in 1:1 EtOAc/CHCl3)

Sources & evidence

ORD record
ord-c3b54032bd3f4e788a295bfc49dc6a27
Source dataset
uspto-grants-2004_11
Patent number
US06825188B2

Reaction notes

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