Water → HCID 57941517, compound

HRID 1437921Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16](=[O:17])[C:15]2[C@@H:14]3[C:18]([CH3:20])([CH3:19])[C@@:11]([CH3:21])([CH2:12][CH2:13]3)[C:10]=2[NH:9]1.IC.O.[C:25](=O)(O)[O-].[Na+]>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16](=[O:17])[C:15]2[C@@H:14]3[C:18]([CH3:20])([CH3:19])[C@@:11]([CH3:21])([CH2:12][CH2:13]3)[C:10]=2[N:9]1[CH3:25]

Participants

Conditions

Temperature: 98 °C

Procedure

A mixture of a (4S,7R)-2-(2-fluoro-phenyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 12; 1.06 g, 3.7 mmol) and iodomethane (450 μL, 7.2 mmol) in N,N-dimethylformamide (20 mL) in a sealed tube was heated to 98° C. and stirred for 5 h. The reaction mixture was allowed to cool and water (20 mL) and saturated sodium bicarbonate solution (200 mL) were added. The solution was extracted with ethyl acetate (200 mL), and the organic layer was washed with brine (200 mL), dried (sodium sulfate), filtered, and evaporated. The residue was triturated with hexanes (4×5 mL) and the solid was recrystallized twice from ethyl acetate/hexanes to give (4S,7R)-2-(2-fluoro-phenyl)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (451 mg, 41%) as white needles. ES(+)-MS (M+H) 301.

Workup

temperatureto cool
extractionThe solution was extracted with ethyl acetate (200 mL)
washthe organic layer was washed with brine (200 mL)
dry with materialdried (sodium sulfate)
filtrationfiltered
customevaporated
customThe residue was triturated with hexanes (4×5 mL)
customthe solid was recrystallized twice from ethyl acetate/hexanes

Sources & evidence

ORD record: ord-c10e80f88f30403eb3ffb40c9f12ec48
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622492B2

Reaction notes

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