2-(Benzyloxy)-1-(3-butenyl)-3-methoxybenzene → (2S)-4-[2-(benzyloxy)-3-methoxyphenyl]-1,2-butanediol

HRID 47945

Reaktionsgleichung

Reaktionsgleichung von HRID 47945
CC[C@H]1[C@H]2C[C@H]([C@H](OC3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[C:28]([O:35][C@H:36]([C:47]4[CH:56]=[CH:55]N=C5[C:48]=4[CH:49]=[C:50]([O:57]C)[CH:51]=C5)[C@@H:37]4N5C[C@H](CC)[C@@H](CC5)[CH2:38]4)=NN=3)C3C=CN=C4C=3C=C(OC)C=C4)N(CC2)C1.[CH2:59]([O:66]C1C(OC)=CC=CC=1CCC=C)C1C=CC=CC=1.O.C([OH:84])(C)(C)C>>[CH2:28]([O:35][C:36]1[C:37]([O:66][CH3:59])=[CH:38][CH:55]=[CH:56][C:47]=1[CH2:48][CH2:49][C@H:50]([OH:57])[CH2:51][OH:84])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Komponenten

4

Edukt 3

HCID 121149552-(Benzyloxy)-1-(3-butenyl)-3-methoxybenzeneHCID 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)phthalazineHCID 714019492-Methylpropan-2-ol--water (1/1)2×

Produkt 1

HCID 11335655(2S)-4-[2-(benzyloxy)-3-methoxyphenyl]-1,2-butanediolAusbeute 92 %

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a suspension of AD-mix-α (63.28 g) in water:tert-butyl alcohol (1:1, 300 mL) cooled to 0° C. is slowly added via an addition funnel to a solution of 2-(benzyloxy)-1-(3-butenyl)-3-methoxybenzene (12.13 g, 45.2 mmol) in water:tert-butyl alcohol (1:1, 300 mL). The reaction mixture is allowed to stir at room temperature for 12 h. The reaction mixture is quenched by the addition of sodium sulfite. The reaction mixture is diluted with water (500 mL) and ethyl acetate (500 mL). The aqueous phase is separated and extracted with ethyl acetate (2×200 mL). The combined organic extracts are washed with aqueous sodium chloride (400 mL), dried (magnesium sulfate) and the solvent is removed in vacuo to give a crude oil. Purification by flash column chromatography (silica, ethyl acetate:hexanes 4:1) provides 12.57 g (92%, 40% ee) of (2S)-4-[2-(benzyloxy)-3-methoxyphenyl]-1,2-butanediol as a colorless oil. [α]D25=−3.04 (c 10.2 in methanol, 40% ee); Rf=0.72 (silica, ethyl acetate:hexanes 4:1); Anal. Calcd. for C18H22O4.0.1H2O: C, 71.08; H, 7.36. Found: C, 70.95; H, 7.33.

Aufarbeitung

  1. customThe reaction mixture is quenched by the addition of sodium sulfite
  2. additionThe reaction mixture is diluted with water (500 mL) and ethyl acetate (500 mL)
  3. customThe aqueous phase is separated
  4. extractionextracted with ethyl acetate (2×200 mL)
  5. washThe combined organic extracts are washed with aqueous sodium chloride (400 mL)
  6. dry with materialdried (magnesium sulfate)
  7. customthe solvent is removed in vacuo
  8. customto give a crude oil
  9. customPurification by flash column chromatography (silica, ethyl acetate:hexanes 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-68f39b83910e4c828d89441aa4ece81f
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06700001B2

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