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

HRID 344049ノート

反応式

HRID 344049 の反応式
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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3ed35035f25c49fc9c862e966a0669e4
出典データセット
uspto-grants-1999_01
特許番号
US05863918

反応ノート

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