Triethylamine → 5-Hydroxymethyl-6-(2-trifluoromethylsulfonyloxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline

HRID 909309Notes

Reaction equation

[OH:1][CH2:2][C:3]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[OH:19])=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([CH3:22])=[CH:6][C:7]([CH3:21])([CH3:20])[NH:8]2.C(N(CC)CC)C.[F:30][C:31]([F:37])([F:36])[S:32](Cl)(=[O:34])=[O:33]>ClCCl.C(Cl)(Cl)Cl>[OH:1][CH2:2][C:3]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][S:32]([C:31]([F:37])([F:36])[F:30])(=[O:34])=[O:33])=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([CH3:22])=[CH:6][C:7]([CH3:21])([CH3:20])[NH:8]2

Participants

Conditions

Temperature: 0 °C

Procedure

5-Hydroxymethyl-6-(2-hydroxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Reference Compound No. 3-1,293 mg, 0.992 mmol) was dissolved in anhydrous dichloromethane (5 mL) and then triethylamine (167 μL, 1.20 mmol) and trifluoromethanesulfonyl chloride (106 μL, 0.996 mmol) were added thereto at 0° C. After the reaction mixture was stirred at 0° C. for 1 hour, it was diluted with chloroform (20 mL). The whole was washed with saturated aqueous NaHCO3 solution (20 mL) and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (177 mg) as an orange solid. (Yield 42%)

Workup

customat 0° C
washThe whole was washed with saturated aqueous NaHCO3 solution (20 mL)
customthe solvent was removed under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record: ord-363e7c4ce3414164848876eec1a24e02
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017775B2

Reaction notes

Loading…