tert-Butanol → (1R,2S)-1,2-dihydroxy-1-(4,5-diphenyloxazol-2-yl)cyclohexane

HRID 1067109Notes

Reaction equation

HRID 1067109 reaction equation
[CH3:1][CH2:2][C@H:3]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(OC)C=C4)N(CC2)C1.CS(N)(=O)=O.[C:64]1([C:70]2[N:71]=C(C3CCCCC=3)[O:73][C:74]=2[C:75]2[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=2)[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1.S([O-])([O-])=[O:88].[Na+].[Na+].[CH3:93][C:94]([OH:97])([CH3:96])[CH3:95]>O>[OH:97][C@:94]1([C:96]2[O:73][C:74]([C:75]3[CH:76]=[CH:77][CH:78]=[CH:79][CH:80]=3)=[C:70]([C:64]3[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=3)[N:71]=2)[CH2:95][CH2:3][CH2:2][CH2:1][C@@H:93]1[OH:88]

Participants

7

Reactant 5

HCID 6386tert-ButanolHCID 24437Sodium SulfiteHCID 72879MethanesulfonamideHCID 184591392-(1-Cyclohexenyl)-4,5-diphenyloxazoleHCID 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 57102465(1R,2S)-1,2-dihydroxy-1-(4,5-diphenyloxazol-2-yl)cyclohexane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of AD-mix-α® (30 g) in a mixture of t-BuOH (600 ml) and water (600 ml) was stirred for 1 hour, and then methanesulfonamide (9.3 g) and 1-(4,5-diphenyloxazol-2-yl)-1-cyclohexene added to the solution at room temperature. After being stirred for 20 hours at the same temperature, sodium sulfite (60 g) was added, and the mixture was stirred for 30 minutes. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with 1N-HCl solution, sat. NaHCO3 and brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by chromatography on silica gel to afford (1R,2S)-1,2-dihydroxy-1-(4,5-diphenyloxazol-2-yl)cyclohexane (30 g).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred for 30 minutes
  3. customThe mixture was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with 1N-HCl solution, sat. NaHCO3 and brine
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo
  7. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-27b7ec55874c49e59f11a6abb4b69419
Source dataset
uspto-grants-2001_06
Patent number
US06245790B1

Reaction notes

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