Hydrogen Peroxide → HCID 58817704, compound

HRID 456564Notes

Reaction equation

HRID 456564 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:18]3[CH:19]=[CH:20][C:21]([F:23])=[CH:22][C:17]=3[O:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N-]C(C)C)(C)C.[Li+].C[O:33]B(OC)OC.OO>O1CCCC1.C(O)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:18]3[CH:19]=[CH:20][C:21]([F:23])=[C:22]([OH:33])[C:17]=3[O:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 8470Trimethyl borateHCID 2724682Lithium diisopropylamideHCID 49760093HCID 49760093, compound

Product 1

HCID 58817704HCID 58817704, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 4-(6-fluoro-benzo[d]isoxazol-3-yl)-piperidine-1-carboxylic acid tert-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 CH2Cl2 (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.

Workup

  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 CH2Cl2 (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 chromatography (1:1; Et2O/Pet. ether)

Sources & evidence

ORD record
ord-838f9a5b04544b2c9e3c109c3bf124aa
Source dataset
uspto-grants-2007_03
Patent number
US07186724B2

Reaction notes

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