Sodium Methoxide → HCID 86709998, compound

HRID 920636Notes

Reaction equation

HRID 920636 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[CH:13]=[C:14]4[C@:19]([C:21]([O:23][CH3:24])=[O:22])([CH2:20][C:11]=3[CH:10]=[N:9]2)[CH2:18][N:17]([S:25]([C:28]2[CH:33]=[C:32]([F:34])[C:31](F)=[C:30]([F:36])[CH:29]=2)(=[O:27])=[O:26])[CH2:16][CH2:15]4)=[CH:4][CH:3]=1.[CH3:37][O-:38].[Na+]>CS(C)=O>[F:34][C:32]1[CH:33]=[C:28]([S:25]([N:17]2[CH2:16][CH2:15][C:14]3[C@:19]([C:21]([O:23][CH3:24])=[O:22])([CH2:20][C:11]4[CH:10]=[N:9][N:8]([C:5]5[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=5)[C:12]=4[CH:13]=3)[CH2:18]2)(=[O:27])=[O:26])[CH:29]=[C:30]([F:36])[C:31]=1[O:38][CH3:37]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86709994HCID 86709994, compound

Product 1

HCID 86709998HCID 86709998, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of (R)-methyl 1-(4-fluorophenyl)-6-((3,4,5-trifluorophenyl)sulfonyl)-4,4a,5,6,7,8-hexahydro-1H-pyrazolo[3,4-g]isoquinoline-4a-carboxylate (150 mg, 0.288 mmol) in dimethyl sulphoxide (4 mL) was added sodium methoxide (25% in methanol) (65.8 μl, 0.288 mmol) dropwise. The reaction mixture was stirred at room temperature for 1 hour, then allowed to stand at room temperature overnight. The crude product was purified by column chromatography on silica gel (gradient: 0-50% ethyl acetate in isohexane) to afford (R)-methyl 6-((3,5-difluoro-4-methoxyphenyl)sulfonyl)-1-(4-fluorophenyl)-4,4a,5,6,7,8-hexahydro-1H-pyrazolo[3,4-g]isoquinoline-4a-carboxylate (150 mg) as a pale yellow solid. LCMS (Method F, ES-API): RT 2.51 min, m+H=534.2.

Workup

  1. waitto stand at room temperature overnight
  2. customThe crude product was purified by column chromatography on silica gel (gradient: 0-50% ethyl acetate in isohexane)

Sources & evidence

ORD record
ord-d6eec6928b7548c3b9e6c4bd6cd70b48
Source dataset
uspto-grants-2016_03
Patent number
US09273047B2

Reaction notes

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