Toluene → (4,5,6,7-Tetrahydro-1H-indazol-4-yl)-carbamic acid benzyl ester

HRID 1013814Notes

Reaction equation

HRID 1013814 reaction equation
[CH2:1]([O:8][C:9](=[O:18])[NH:10][CH:11]1[CH2:16][CH2:15][CH2:14][C:13](=O)[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.C(OC([N:35]([CH3:37])C)N(C)C)(C)(C)C.O.[NH2:39]N>CO>[CH2:1]([O:8][C:9](=[O:18])[NH:10][CH:11]1[CH2:16][CH2:15][CH2:14][C:13]2[NH:39][N:35]=[CH:37][C:12]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 24654Hydrazine hydrate (1:1)HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 10171453HCID 10171453, compound

Product 1

HCID 67316351(4,5,6,7-Tetrahydro-1H-indazol-4-yl)-carbamic acid benzyl esterYield 72.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Stir a mixture of (3-Oxo-cyclohexyl)-carbamic acid benzyl ester (12.3 g, 49.8 mmol), toluene (60 mL) and tert-butoxybis(dimethylamino)methane (9.53 g, 54.77 mmol) at 90° C. for 1.5 hour. Cool the reaction and remove the solvent in vacuo. To the residue, add methanol (60 mL) and hydrazine hydrate (2.74 g, 54.77 mmol). Stir the reaction at room temperature for 3 hours. Remove the solvent in vacuo. To the residue, add ethyl acetate and wash with water. After drying the organic layer over sodium sulfate, filter and concentrate to afford 9.8 g of the title compound with 80% purity.

Workup

  1. temperatureCool
  2. customthe reaction
  3. customremove the solvent in vacuo
  4. stirringStir
  5. customthe reaction at room temperature for 3 hours
  6. customRemove the solvent in vacuo
  7. additionTo the residue, add ethyl acetate
  8. washwash with water
  9. dry with materialAfter drying the organic layer over sodium sulfate
  10. filtrationfilter
  11. concentrationconcentrate

Sources & evidence

ORD record
ord-f840517c2dae4348a2101deda15310de
Source dataset
uspto-grants-2011_07
Patent number
US07981918B2

Reaction notes

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