Sodium Sulfate → HCID 87347838, compound

HRID 2061603Notes

Reaction equation

HRID 2061603 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([S:30]([N:33]2[C:37]3[CH2:38][CH:39]4[N:44]([S:45]([C:48]5[CH:53]=[CH:52][C:51]([Cl:54])=[CH:50][CH:49]=5)(=[O:47])=[O:46])[CH:43]([C:36]=3[CH:35]=[N:34]2)[CH2:42][CH:41]([CH2:55][OH:56])[CH2:40]4)(=[O:32])=[O:31])=[CH:26][CH:25]=1.[Cl:57][C:58]1[CH:63]=[CH:62][C:61]([S:64]([N:67]2[CH:71]=[C:70]3[CH:72]4[N:78]([S:79]([C:82]5[CH:87]=[CH:86][C:85]([Cl:88])=[CH:84][CH:83]=5)(=[O:81])=[O:80])[CH:76]([CH2:77][C:69]3=[N:68]2)[CH2:75][CH:74]([CH2:89][OH:90])[CH2:73]4)(=[O:66])=[O:65])=[CH:60][CH:59]=1.C(=O)(O)[O-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>>[Cl:23][C:24]1[CH:25]=[CH:26][C:27]([S:30]([N:33]2[C:37]3[CH2:38][CH:39]4[N:44]([S:45]([C:48]5[CH:49]=[CH:50][C:51]([Cl:54])=[CH:52][CH:53]=5)(=[O:47])=[O:46])[CH:43]([C:36]=3[CH:35]=[N:34]2)[CH2:42][CH:41]([CH:55]=[O:56])[CH2:40]4)(=[O:32])=[O:31])=[CH:28][CH:29]=1.[Cl:57][C:58]1[CH:59]=[CH:60][C:61]([S:64]([N:67]2[CH:71]=[C:70]3[CH:72]4[N:78]([S:79]([C:82]5[CH:83]=[CH:84][C:85]([Cl:88])=[CH:86][CH:87]=5)(=[O:81])=[O:80])[CH:76]([CH2:77][C:69]3=[N:68]2)[CH2:75][CH:74]([CH:89]=[O:90])[CH2:73]4)(=[O:66])=[O:65])=[CH:62][CH:63]=1

Participants

7

Reactant 5

HCID 24436Sodium SulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium Bicarbonate2×HCID 67303821HCID 67303821, compoundHCID 68528112HCID 68528112, compound

Product 2

HCID 87347838HCID 87347838, compoundYield 87%HCID 87350243HCID 87350243, compound

Procedure

Dess-Martin periodinane (128 mg, 0.304 mmol) was added to a solution of {1,10-bis[(4-chlorophenyl)sulfonyl]-4,5,6,7,8,9-hexahydro-1H-4,8-epiminocycloocta[c]pyrazol-6-yl}methanol and {2,10-Bis[(4-chlorophenyl)sulfonyl]-4,5,6,7,8,9-hexahydro-2H-4,8-epiminocycloocta[c]pyrazol-6-yl}methanol (58) (110 mg, 0.202 mmol) containing sodium bicarbonate (76 mg, 0.912 mmol). The resulting suspension was stirred at room temperature for 2 h after which a mixture of saturated aqueous NaHCO3 and saturated aqueous Na2SO4 (1/1, v/v) was added. The organic phase was dried (Na2SO4), filtered, concentrated and purified by silica gel column chromatography (eluant hexane/EtOAc, 4/1 to 1/1) to give 1,10-bis[(4-chlorophenyl)sulfonyl]-4,5,6,7,8,9-hexahydro-1H-4,8-epiminocycloocta[c]pyrazole-6-carbaldehyde and 2,10-bis[(4-chlorophenyl)sulfonyl]-4,5,6,7,8,9-hexahydro-2H-4,8-epiminocycloocta[c]pyrazole-6-carbaldehyde (59) (95 mg, 0.175 mmol, 87%). MS (ESI) 540.0 (M+H).

Workup

  1. additionv/v) was added
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography (eluant hexane/EtOAc, 4/1 to 1/1)

Sources & evidence

ORD record
ord-aef1ee51d91a4f32919fae005067fb3c
Source dataset
uspto-grants-2012_10
Patent number
US08283358B2

Reaction notes

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