(3-Methyl-but-3-enyloxymethyl)-benzene → (S)-4-(benzyloxy)-2-methylbutane-1,2-diol

HRID 332072노트

반응식

HRID 332072 반응식
CC(=C)C[CH2:4][O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.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:35]C)C=C4)N(CC2)C1.[CH3:72][C:73]([OH:76])([CH3:75])[CH3:74].O>>[CH2:6]([O:5][CH2:4][CH2:72][C@:73]([CH3:75])([OH:76])[CH2:74][OH:35])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

참가 물질

4

반응물 3

HCID 11095166(3-Methyl-but-3-enyloxymethyl)-benzeneHCID 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)

생성물 1

HCID 67205693(S)-4-(benzyloxy)-2-methylbutane-1,2-diol

실험 절차

Compound 1 was added to a solution of AD-mix-α in tBuOH/H2O (1:1) cooled in an ice bath. After TCL monitoring showed the disappearance of the starting material, the reaction was quenched by adding Na2SO3. The aqueous phase was extracted with ethyl acetate three times and the combined organic phase was washed with brine and dried (Na2SO4). The solid was filtered and the solvent was removed. The residue was purified by column chromatography to give compound 2.

후처리

  1. temperaturecooled in an ice bath
  2. customthe reaction was quenched
  3. additionby adding Na2SO3
  4. extractionThe aqueous phase was extracted with ethyl acetate three times
  5. washthe combined organic phase was washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationThe solid was filtered
  8. customthe solvent was removed
  9. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-401cd47f701847db96bc095f71c65c2d
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877796B2

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