Prenderol → HCID 59089977, compound

HRID 1582412Notes

Reaction equation

HRID 1582412 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:9]([OH:12])[C:10]=1[OH:11])=[O:5])[CH3:2].[CH2:25]([C:27]([CH2:32][CH3:33])([CH2:30]O)[CH2:28]O)[CH3:26]>O1CCCC1>[CH2:16]([O:15][C:13]([C:8]1[N:7]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[C:10]2[C:9]=1[O:12][CH2:30][C:27]([CH2:32][CH3:33])([CH2:25][CH3:26])[CH2:28][O:11]2)=[O:14])[CH3:17]

Participants

4

Reactant 2

HCID 8284PrenderolHCID 54682554Diethyl 1-benzyl-3,4-dihydroxy-1H-pyrrole-2,5-dicarboxylate

Product 1

HCID 59089977HCID 59089977, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

ADC01 (2.9 g, 16.9 mmol) was slowly added to a solution of N-benzyl-3,4-dihydroxypyrrole-2,5-dicarboxylic acid diethyl ester (2.6 g, 7.7 mmol), 2,2-diethyl-1,3-propanediol (1.1 g, 8.5 mmol), and PH02 (4.4 g, 16.9 mmol) in dry tetrahydrofuran (150 ml) at 0° C. The reaction mixture was then allowed to warm to 25° C., stirred for 3 h, and then was refluxed for 21 h. The reaction mixture was then allowed to cool to 25° C. and was concentrated by rotary evaporator to remove the tetrahydrofuran. The residue was then diluted with diethyl ether and allowed to stand overnight to enable the tributylphosphine oxide to precipitate out. The tributylphosphine oxide was then removed by filtration and the remaining product was purified by chromatography on silica gel (eluant: ethyl acetate/hexane=3/1) to give 2-benzyl-6,6-diethyl-6, 7-dihydro-2H,5H-4,8-dioxa-2-aza-azulene-1,3-dicarboxylic acid diethyl ester as a colourless oil in 2.5 g (75%) yield as characterized by 1H NMR, 13C NMR, HRMS, and elemental analysis.

Workup

  1. temperaturewas refluxed for 21 h
  2. temperatureto cool to 25° C.
  3. concentrationwas concentrated by rotary evaporator
  4. customto remove the tetrahydrofuran
  5. additionThe residue was then diluted with diethyl ether
  6. waitto stand overnight
  7. customto precipitate out
  8. customThe tributylphosphine oxide was then removed by filtration
  9. customthe remaining product was purified by chromatography on silica gel (eluant: ethyl acetate/hexane=3/1)

Sources & evidence

ORD record
ord-fd63a991405d48cd90375b9a0256a5ed
Source dataset
uspto-grants-2004_05
Patent number
US06734312B2

Reaction notes

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