Dimethyl Sulfate → HCID 57941330, compound

HRID 1437926Notes

Reaction equation

HRID 1437926 reaction equation
S(OC)(O[CH3:5])(=O)=O.[F:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:23](=[O:24])[C:22]3[C@@H:21]4[C:25]([CH3:27])([CH3:26])[C@@:18]([CH3:28])([CH2:19][CH2:20]4)[C:17]=3[NH:16]2)=[CH:11][CH:10]=1>[OH-].[Na+]>[F:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:23](=[O:24])[C:22]3[C@@H:21]4[C:25]([CH3:27])([CH3:26])[C@@:18]([CH3:28])([CH2:19][CH2:20]4)[C:17]=3[N:16]2[CH3:5])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 57941456HCID 57941456, compound2×

Product 1

HCID 57941330HCID 57941330, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of dimethyl sulfate (1.1 mL, 11.6 mmol) and (4S,7R)-2-(4-fluoro-phenyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 13; 1.65 g, 5.8 mmol) in 1 M NaOH (25 mL) was heated at 50 degrees overnight, and then allowed to stand at room temperature over the weekend. The precipitate was filtered off, washed with water, and recrystallized from ethyl acetate to give (4S,7R)-2-(4-fluoro-phenyl)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (239 mg, 14%) as a white solid. ES(+)-MS (M+H) 301.

Workup

  1. temperaturewas heated at 50 degrees overnight
  2. customto stand at room temperature over the weekend
  3. filtrationThe precipitate was filtered off
  4. washwashed with water
  5. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-f8694aeae448480298ba4399a9d396a0
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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