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

HRID 963719ノート

反応式

HRID 963719 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
  5. dry with materialHCl solution, sat. NaHCO3, and brine, dried 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-8e9535d2936742118ef84570169733dd
出典データセット
uspto-grants-1998_06
特許番号
US05763489

反応ノート

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