tert-Butanol → (+/-)-3-[2-(Benzyloxy)-4-methoxyphenyl]propane-1,2-diol

HRID 2115902Notes

Reaction equation

HRID 2115902 reaction equation
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][CH3:58])[CH:51]=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C(OC)C=C4)N(CC2)C1.[C:59]([OH:63])(C)(C)C.C(C1C=CC([O:73]C)=CC=1OCC1C=CC=CC=1)C=C>O>[CH2:28]([O:35][C:36]1[CH:51]=[C:50]([O:57][CH3:58])[CH:49]=[CH:48][C:47]=1[CH2:56][CH:55]([OH:73])[CH2:59][OH:63])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 6386tert-Butanol2×HCID 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 689665561-Allyl-2-(benzyloxy)4-methoxybenzene

Product 1

HCID 68966303(+/-)-3-[2-(Benzyloxy)-4-methoxyphenyl]propane-1,2-diolYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of AD-mix-α (156.55 g) in water:tert-butyl alcohol (1:1,800 mL) cooled to 0° C. was slowly added via an addition funnel a solution of 1-allyl-2-(benzyloxy)-4-methoxybenzene (28.44 g, 0.112 mol) in water:tert-butyl alcohol (1:1,200 mL) and the reaction mixture was allowed to stir at 0° C. for 12 h. The reaction mixture was quenched by the addition of sodium sulfite. The reaction mixture was diluted with water (500 mL) and ethyl acetate (500 mL). The aqueous phase was separated and extracted with ethyl acetate (2×200 mL). The combined organic extracts were washed with saturated aqueous sodium chloride (400 mL), dried (magnesium sulfate) and the solvent was removed in vacuo to give a crude oil. Purification by flash column chromatography (silica, ethyl acetate:hexanes 3:2) gave 30.50 g (95%, 27% ee) of (±)-3-[2-(benzyloxy)-4-methoxyphenyl]propane-1,2-diol as a white crystalline solid. mp 82-86° C.; Anal. calcd. for C17H20O4: C, 70.81; H, 6.99. Found: C, 70.78; H, 7.16.

Workup

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

Sources & evidence

ORD record
ord-a872e3e00e6d408ca88a10ac2d921795
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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