Tetrahydrofuran → (3-((Dimethylamino)methyl)-5-fluorophenyl)methanol

To a solution of methyl 3-[(dimethylamino)methyl]-5-fluorobenzoate (0.14 g, 0.66 mmol, Example 33, Step 3) in Ether (4 mL) at 0° C. in an ice bath was added dropwise 1.0M lithium tetrahydroaluminate in THF (1.32 mL, 1.32 mmol). The reaction was allowed to warm to room temperature and stirred for 1.5 hours. The reaction mixture was re-cooled in an ice bath and methanol, followed by 1N NaOH, were added to quench the reaction. The product was extracted from the reaction mixture with three portions of ethyl acetate. The combined extracts were dried over sodium sulfate, decanted and concentrated, to afford product which was used without further purification (0.100 g, 82%). 1H NMR (300 MHz, CD3OD): δ 7.13-6.94 (m, 3H), 4.59 (s, 2H), 3.47 (s, 2H), 2.24 (s, 6H); 19F NMR (282 MHz, CD3OD): δ−116.41 (t, 1F); LCMS (M+H)+: 184.0.

1. temperatureThe reaction mixture was re-cooled in an ice bath
2. additionwere added
3. customto quench
4. customthe reaction
5. extractionThe product was extracted from the reaction mixture with three portions of ethyl acetate
6. dry with materialThe combined extracts were dried over sodium sulfate
7. customdecanted
8. concentrationconcentrated
9. customto afford product which
10. customwas used without further purification (0.100 g, 82%)

ORD record

ord-2a9dc1181cc3428e91dcdb13713748f0

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08933085B2