Hydrogen Peroxide → HCID 58817704, compound

Temperature

-78 °C

To a stirred solution of 4-(6-fluoro-benzo[d]isoxazol-3-yl)-piperidine-1-carboxylic acid ter-butyl ester (1.00 g, 3.13 mmol) in dry tetrahydrofuran (31.3 mL) cooled to −78° C. was added lithium diisopropylamide (1.72 mL, 3.35 mmoles). The resulting solution was stirred at −78° C. for 2 hours when trimethylborate (0.44 mL, 3.84 mmoles) was added. The resulting solution was stirred at −78° C. for 1 hour then was allowed to warm to room temperature over 3 hours when hydrogen peroxide (2.00 mL) and acetic acid (1.00 mL) were added. The resulting mixture was stirred at room temperature overnight when the mixture was quenched with saturated NH4Claq (20 mL) and 10% HClaq (20 mL). The resulting mixture was extracted with CH-2C12 (4×50 mL). The combined extracts were washed with brine (50 mL), dried (MgSO4), filtered and evaporated. The residue was separated via column:chromatography (1:1; Et2O/Pet. ether) yielding 0.619 g (59%) of the phenol as a white, crystalline solid, mp 169-170° C. Analysis calculated for C17H21N2FO4; 60.70% C, 6.29% H, 8.33% N. Found: 60.72% C, 6.15% H, 8.22% N.

1. additionwas added
2. additionwere added
3. stirringThe resulting mixture was stirred at room temperature overnight when the mixture
4. customwas quenched with saturated NH4Claq (20 mL) and 10% HClaq (20 mL)
5. extractionThe resulting mixture was extracted with CH-2C12 (4×50 mL)
6. washThe combined extracts were washed with brine (50 mL)
7. dry with materialdried (MgSO4)
8. filtrationfiltered
9. customevaporated
10. customThe residue was separated via column

ORD record

ord-4e2433c69b334ab897f5417ec14468eb

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07772252B2