Sodium Hydroxide → HCID 67110676, compound

HRID 2076370Notes

Reaction equation

HRID 2076370 reaction equation
[Cl:1][C:2]1[C@H:3]([OH:30])[C@H:4]2[CH2:29][C@@:7]3([C:18]=1[C:17]1[CH:16]=[CH:15][C:14]4[N:13](S(C5C=CC(C)=CC=5)(=O)=O)[N:12]=[CH:11][C:10]=4[C:9]=1[CH2:8]3)[CH2:6][CH2:5]2.Cl[C:32]1[C@H](O)[C@H]2C[C@@]3(C=1C1C=CC4C(=CN(S(C5C=CC(C)=CC=5)(=O)=O)N=4)C=1C3)CC2.S([O-])([O-])(=O)=O.[Ca+2].[OH-].[Na+]>CI.ClCCl.[Ag-]=O>[Cl:1][C:2]1[C@H:3]([O:30][CH3:32])[C@H:4]2[CH2:29][C@@:7]3([C:18]=1[C:17]1[CH:16]=[CH:15][C:14]4[NH:13][N:12]=[CH:11][C:10]=4[C:9]=1[CH2:8]3)[CH2:6][CH2:5]2

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 24497Calcium SulfateHCID 67110511HCID 67110511, compoundHCID 67110704HCID 67110704, compound

Product 1

HCID 67110676HCID 67110676, compound

Reagents, catalysts & solvents 3

HCID 178418778HCID 178418778, compoundCatalystHCID 6328Methyl iodideSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of (7R,8R,10aS)-6-chloro-3-[(4-methylphenyl)sulfonyl]-3,7,8,9,10,11-hexahydro-8,10a-methanoazuleno[2,1-e]indazol-7-ol and (7R,8R,10aS)-6-chloro-2-[(4-methylphenyl)sulfonyl]-2,7,8,9,10,11-hexahydro-8,10a-methanoazuleno[2,1-e]indazol-7-ol prepared as described in Step 2 (0.040 g, 0.091 mmol) was dissolved in methyl iodide (2 mL) and silver(I) oxide (0.080 g, 0.35 mmol) and calcium sulfate (0.080 g, 0.59 mmol) were added. The mixture was stirred at room temperature for two days. The reaction mixture was diluted with dichloromethane and filtered through a pad of silica gel, rinsing with EtOAc. The solvent was evaporated under reduced pressure and the residue was dissolved in ethanol (2 mL) and treated with 1N aqueous sodium hydroxide (0.30 mL, 0.30 mmol). After 2 hours, the reaction mixture was diluted with dichloromethane and dried over MgSO4. The solution was filtered through a pad of silica gel and the solvent was evaporated under reduced pressure. The residue was chromatographed on silica gel (elution with 1:1 EtOAc/hexanes) to yield (7R,8R,10aS)-6-chloro-7-methoxy-3,7,8,9,10,11-hexahydro-8,10a-methanoazuleno[2,1-e]indazole.

Workup

  1. customprepared
  2. filtrationfiltered through a pad of silica gel
  3. washrinsing with EtOAc
  4. customThe solvent was evaporated under reduced pressure
  5. dissolutionthe residue was dissolved in ethanol (2 mL)
  6. waitAfter 2 hours
  7. dry with materialdried over MgSO4
  8. filtrationThe solution was filtered through a pad of silica gel
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was chromatographed on silica gel (elution with 1:1 EtOAc/hexanes)

Sources & evidence

ORD record
ord-a17dc783f8cc448e8e412c4fcff37a21
Source dataset
uspto-grants-2011_04
Patent number
US07923568B2

Reaction notes

Loading…