Isoxazole, 4-(chloromethyl)-3,5-dimethyl- → HCID 57149884, compound

HRID 1779975Notes

Reaction equation

C([Li])CCC.[CH3:6][O:7][C:8]1[C@@H:9]([CH:16]([CH3:18])[CH3:17])[N:10]=[C:11]([O:14][CH3:15])[CH2:12][N:13]=1.Cl[CH2:20][C:21]1[C:22]([CH3:27])=[N:23][O:24][C:25]=1[CH3:26]>CCCCCC.C1COCC1>[CH3:6][O:7][C:8]1[C@@H:9]([CH:16]([CH3:18])[CH3:17])[N:10]=[C:11]([O:14][CH3:15])[C@H:12]([CH2:20][C:21]2[C:22]([CH3:27])=[N:23][O:24][C:25]=2[CH3:26])[N:13]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A 1.55M solution of butyllithium (10 ml, 15.5 mmol) in hexane was added by syringe to a stirred solution of (2R)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine (2.85 g, 15.5 mmol) in THF (50 ml) at -78° C. and the solution stirred for 1 hour at -78° C. A solution of 4- chloromethyl-3,5-dimethylisoxazole (2.34 g, 16 mmol) in THF (10 ml) was added gradually and the stirring continued overnight. The solvent was removed under reduced pressure, the residue dissolved in ethyl acetate (50 ml) and extracted with phosphate buffer (pH 7). The water phase was extracted twice with ethyl acetate (2×20 ml). The organic layer was dried (MgSO4), solvent evaporated under reduced pressure and the residue purified by flash chromatography (diethyl ether/hexane 4/1, silica gel).

Workup

customthe stirring continued overnight
customThe solvent was removed under reduced pressure
dissolutionthe residue dissolved in ethyl acetate (50 ml)
extractionextracted with phosphate buffer (pH 7)
extractionThe water phase was extracted twice with ethyl acetate (2×20 ml)
dry with materialThe organic layer was dried (MgSO4), solvent
customevaporated under reduced pressure
customthe residue purified by flash chromatography (diethyl ether/hexane 4/1, silica gel)

Sources & evidence

ORD record: ord-8f21594c9ab04271b2970f2111af603b
Source dataset: uspto-grants-1997_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05629293

Reaction notes

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