2,6-Dimethylcyclohexanol → HCID 117642487, compound

HRID 1507744Notes

Reaction equation

HRID 1507744 reaction equation
[H-].[Na+].[CH3:3][CH:4]1[CH2:9][CH2:8][CH2:7][CH:6]([CH3:10])[CH:5]1[OH:11].[CH2:12]([O:19][C:20]1[C:24]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:23]([C:33](=[O:37])[N:34]([CH3:36])[CH3:35])[N:22]([C:38]2[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=2)[C:21]=1[C:46](OCC)=[O:47])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C=O)C>[CH2:12]([O:19][C:20]1[C:24]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:23]([C:33](=[O:37])[N:34]([CH3:35])[CH3:36])[N:22]([C:38]2[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=2)[C:21]=1[C:46]([O:11][CH:5]1[CH:6]([CH3:10])[CH2:7][CH2:8][CH2:9][CH:4]1[CH3:3])=[O:47])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 214282,6-DimethylcyclohexanolHCID 24758Sodium hydrideHCID 89610459HCID 89610459, compound

Product 1

HCID 117642487HCID 117642487, compoundYield 30.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Sodium hydride (60 wt % in oil) (78 mg, 1.95 mmol) was added to a stirred solution of 2,6-dimethylcyclohexanol (250 mg, 1.95 mmol) in DMF (1.95 mL). The mixture was heated at 60° C. for 10 min and then ethyl 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (6) (206 mg, 0.39 mmol) was added in one portion. The reaction was allowed to stir at 70° C. for 16 h. The cooled reaction mixture was filtered through Celite, and the filtrate diluted with EtOAc (20 mL) and washed with water (3×10 mL), the organic layer was dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by silica gel chromatography (12 g, 0.5% MeOH (1% NH3) in DCM) to afford 2,6-dimethylcyclohexyl 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (45) (73 mg, 20%) as a brown oil. m/z 611 (M+H)+ (ES+)

Workup

  1. customThe cooled reaction mixture
  2. filtrationwas filtered through Celite
  3. additionthe filtrate diluted with EtOAc (20 mL)
  4. washwashed with water (3×10 mL)
  5. dry with materialthe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by silica gel chromatography (12 g, 0.5% MeOH (1% NH3) in DCM)

Sources & evidence

ORD record
ord-a367bc4420a84cb09f281c8fb310e0c6
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

Loading…