Water → (1S,2R)-1,2-dihydroxy-2-ethoxycarbonyl-5-t-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene

HRID 344049Notes

Reaction equation

HRID 344049 reaction equation
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:22]C)C=C4)N(CC2)C1.CS(N)(=O)=O.[CH2:64]([O:66][C:67]([C:69]1[CH2:78][CH2:77][C:76]2[C:71](=[CH:72][CH:73]=[CH:74][C:75]=2[O:79][Si:80]([C:93]([CH3:96])([CH3:95])[CH3:94])([C:87]2[CH:92]=[CH:91][CH:90]=[CH:89][CH:88]=2)[C:81]2[CH:86]=[CH:85][CH:84]=[CH:83][CH:82]=2)[CH:70]=1)=[O:68])[CH3:65].S([O-])([O-])=O.[Na+].[Na+].[OH2:103]>C(O)(C)(C)C>[OH:103][C@H:70]1[C:71]2[C:76](=[C:75]([O:79][Si:80]([C:93]([CH3:95])([CH3:94])[CH3:96])([C:87]3[CH:88]=[CH:89][CH:90]=[CH:91][CH:92]=3)[C:81]3[CH:86]=[CH:85][CH:84]=[CH:83][CH:82]=3)[CH:74]=[CH:73][CH:72]=2)[CH2:77][CH2:78][C@:69]1([OH:22])[C:67]([O:66][CH2:64][CH3:65])=[O:68]

Participants

7

Reactant 5

HCID 962WaterHCID 24437Sodium SulfiteHCID 72879MethanesulfonamideHCID 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 545044522-Ethoxycarbonyl-5-t-butyldiphenylsilyloxy-3,4-dihydronaphthalene

Product 1

HCID 54371121(1S,2R)-1,2-dihydroxy-2-ethoxycarbonyl-5-t-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A solution of AD-mix-α (trade name, Aldrich) (9.2 g) in a mixture of t-butyl alcohol (30 ml) and water (30 ml) was stirred for 1 hour and then methanesulfonamide (0.62 g) and 2-ethoxycarbonyl-5-t-butyldiphenylsilyloxy-3,4-dihydronaphthalene (3.0 g) were added to the solution at room temperature. After being stirred for 20 hours at the same temperature, sodium sulfite (9.0 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 (1S,2R)-1,2-dihydroxy-2-ethoxycarbonyl-5-t-butyldiphenylsilyloxy-1,2,3,4-tetrahydronaphthalene (3.1 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-3ed35035f25c49fc9c862e966a0669e4
Source dataset
uspto-grants-1999_01
Patent number
US05863918

Reaction notes

Loading…