Triphenylphosphine → Ethyl (2R)-2-{4-[5-methyl-1-(4-pentylphenylpropyl)-1H-pyrrol-2-yl]phenoxy}-3-phenylpropanoate

HRID 1072719Notes

Reaction equation

HRID 1072719 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:12][CH:11]=2)[C:5]([C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)=[CH:4][CH:3]=1.O[C@@H:29]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:30]([O:32][CH2:33][CH3:34])=[O:31].N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.O>[CH3:1][C:2]1[N:6]([CH2:7][CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:12][CH:11]=2)[C:5]([C:21]2[CH:22]=[CH:23][C:24]([O:27][C@H:29]([CH2:35][C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:25][CH:26]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 9877619Ethyl phenyllactate, (-)-HCID 697326774-[5-Methyl-1-(4-pentylphenylpropyl)-1H-pyrrol-2-yl]phenol

Product 1

HCID 86759769Ethyl (2R)-2-{4-[5-methyl-1-(4-pentylphenylpropyl)-1H-pyrrol-2-yl]phenoxy}-3-phenylpropanoateYield 13%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of 4-[5-methyl-1-(4-pentylphenylpropyl)-1H-pyrrol-2-yl]phenol (1.3 g, 3.6 mmol), ethyl (S)-2-hydroxy-3-phenylpropanoate (1.05 g, 5.4 mmol), 1,1′-(azodicarbonyl)dipiperidine (1.36 g, 5.4 mmol) and triphenylphosphine (1.42 g, 5.4 mmol) in toluene (40 ml) was stirred at 80° C. for 12 hours. The reaction solution was poured into water and extracted with ethyl acetate, and the extract was washed with saturated brine and dried over magnesium sulfate anhydride. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=15:1) to give the object compound as an oily substance. 250 mg, (yield 13%)

Workup

  1. extractionextracted with ethyl acetate
  2. washthe extract was washed with saturated brine
  3. dry with materialdried over magnesium sulfate anhydride
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=15:1)
  6. customto give the object compound as an oily substance

Sources & evidence

ORD record
ord-88a18250dfd94e46a115c1d9cd347225
Source dataset
uspto-grants-2005_06
Patent number
US06911468B2

Reaction notes

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