Hydrogen Peroxide → HCID 10681490, compound

HRID 1816088Notes

Reaction equation

HRID 1816088 reaction equation
IC1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4]C=1.[C:10]([O:14][CH2:15][CH3:16])(=[O:13])C=C.CCN(CC)CC.CC[C@H]1[C@H]2C[C@H]([C@H](OC3C4C(=CC=CC=4)C(O[C@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C([O:45]C)C=C4)N(CC2)C1.CN1CCOCC1.OO.[CH2:91]([OH:95])[CH2:92][CH2:93][CH3:94].O>>[OH:95][C@H:91]([C@@H:92]([OH:45])[C:93]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:94]=1)[C:10]([O:14][CH2:15][CH3:16])=[O:13]

Participants

8

Reactant 7

HCID 784Hydrogen PeroxideHCID 79724-MethylmorpholineHCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 696764-IodoanisoleHCID 22253497Water butanolHCID 510036741-((1R)-((2R,4R,5S)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)-4-((1R)-((2R,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)phthalazine

Product 1

HCID 10681490HCID 10681490, compoundYield 92%

Procedure

LDH-PdOsW (0.4 g, 0.1 mmol), 4-iodoanisole (10 mmol), ethyl acrylate (10 mmol) and Et3N (11 mmol) were stirred at 70° C. for 16 h under nitrogen atmosphere. After completion of the Heck coupling, the heating was stopped and the reaction was allowed to reach room temperature. A mixture of (DHQ)2PHAL (7.8 mg, 0.1 mmol) and NMM (0.5 g, 5 mmol) in BuOH—H2O (5:1, 50 mL) was added in one portion to the reaction flask under stirring. H2O2 (30% aqueous, 15 mmol) was then slowly added over 15 h using a syringe pump. After the addition was complete, the stirring was continued for an additional 1 h and the catalyst was filtered and washed with ethyl acetate (100 mL). After removal of the solvent, thus obtained crude material was chromatographed on silica gel using hexane/ethyl acetate (1:1) as eluant to afford ethyl (2R,3S)-2,3-dihydroxy-3-(4-methoxyphenyl)propionate (92% yield).

Workup

  1. customto reach room temperature
  2. additionwas added in one portion to the reaction flask
  3. additionAfter the addition
  4. filtrationthe catalyst was filtered
  5. washwashed with ethyl acetate (100 mL)
  6. customAfter removal of the solvent
  7. customthus obtained crude material
  8. customwas chromatographed on silica gel

Sources & evidence

ORD record
ord-5018fd94d5af4c68ab4456b7e2c79499
Source dataset
uspto-grants-2005_04
Patent number
US06881839B2

Reaction notes

Loading…