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

HRID 344049노트

반응식

HRID 344049 반응식
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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6386tert-Butanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3ed35035f25c49fc9c862e966a0669e4
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05863918

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