Ethyl Bromide → (1R,7S)-3-ethyl-1,10,10-trimethyl-4-phenyl-3,4-diazatricyclo[5.2.1.02,6]dec-2(6)-en-5-one

HRID 1437909Notes

Reaction equation

HRID 1437909 reaction equation
Br[CH2:2][CH3:3].C(=O)([O-])[O-].[K+].[K+].[C:10]1([N:16]2[C:24](=[O:25])[C:23]3[C@@H:22]4[C:26]([CH3:28])([CH3:27])[C@@:19]([CH3:29])([CH2:20][CH2:21]4)[C:18]=3[NH:17]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CC(C)=O.CO>[CH2:2]([N:17]1[C:18]2[C@@:19]3([CH3:29])[C:26]([CH3:28])([CH3:27])[C@H:22]([CH2:21][CH2:20]3)[C:23]=2[C:24](=[O:25])[N:16]1[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH3:3]

Participants

6

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 57941335(4s,7r)-2-Phenyl-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one2×

Product 1

HCID 57941389(1R,7S)-3-ethyl-1,10,10-trimethyl-4-phenyl-3,4-diazatricyclo[5.2.1.02,6]dec-2(6)-en-5-oneYield 9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 887MethanolSolvent

Procedure

A mixture of bromoethane (1.05 mL, 14.1 mmol), potassium carbonate (3.58 g, 25.9 mmol), and (4S,7R)-2-phenyl-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 6; 1.74 g, 6.5 mmol) in acetone (20 mL) and methanol (3 mL) was stirred at room temperature over the weekend then the solvent was evaporated and the residue was partitioned between water and dichloromethane. The organic layer was evaporated, and the residue was chromatographed (0-50% ethyl acetate/hexanes) and recrystallized from ethyl acetate to give (4S,7R)-1-ethyl-7,8,8-trimethyl-2-phenyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (168 mg, 9%) as a white solid. APCI-MS (M+H) 297.

Workup

  1. customthe solvent was evaporated
  2. customthe residue was partitioned between water and dichloromethane
  3. customThe organic layer was evaporated
  4. customthe residue was chromatographed (0-50% ethyl acetate/hexanes)
  5. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ef81de9b11db436ea4f9f230b18c55ea
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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