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

HRID 2305215Notes

Reaction equation

HRID 2305215 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+].[C:93]([OH:97])([CH3:96])([CH3:95])[CH3:94]>O>[OH:97][C@:93]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:94]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-butanol (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 stirring the mixture 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 EtOAc and water. The organic layer was washed with 1N-hydrochloric acid solution, saturated sodium hydrogencarbonate and brine, dried over magnesium sulfate 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 EtOAc and water
  4. washThe organic layer was washed with 1N-hydrochloric acid solution, saturated sodium hydrogencarbonate and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-fd34953ddac64e40aeb8c91e3cad3453
Source dataset
uspto-grants-2002_08
Patent number
US06437146B1

Reaction notes

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