Hydrochloric Acid → HCID 118622795, compound

HRID 2202316Notes

Reaction equation

HRID 2202316 reaction equation
[CH3:1][O:2][C:3]1[CH:34]=[CH:33][C:6]([CH2:7][N:8]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[C:9]2[CH:14]=[C:13]([F:15])[C:12]([C:16]([CH3:22])([CH3:21])[C:17](OC)=[O:18])=[C:11]([F:23])[CH:10]=2)=[CH:5][CH:4]=1.CC(C[AlH]CC(C)C)C.C1COCC1.Cl.O>C1COCC1.C(OCC)(=O)C.CCCCCC>[CH3:32][O:31][C:28]1[CH:27]=[CH:26][C:25]([CH2:24][N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:34][CH:33]=2)[C:9]2[CH:10]=[C:11]([F:23])[C:12]([C:16]([CH3:22])([CH3:21])[CH2:17][OH:18])=[C:13]([F:15])[CH:14]=2)=[CH:30][CH:29]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 118622733HCID 118622733, compoundHCID 131729343Dibal-H thf2×

Product 1

HCID 118622795HCID 118622795, compoundYield 64.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 2-(4-(bis(4-methoxybenzyl)amino)-2,6-difluorophenyl)-2-methylpropanoate (2.17 g, 4.62 mmol) in THF (30 mL) was added 1M DIBAL-H/THF solution (13.87 mL, 13.87 mmol) at 0° C., and the mixture was stirred at 0° C. for 5 hr. 1M DIBAL-H/THF solution (1.0 mL, 1.0 mmol) was added again thereto at 0° C., and the mixture was stirred at 0° C. for 1.5 hr. To the reaction mixture were added 1N hydrochloric acid and water, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 3→50% ethyl acetate/hexane), and then silica gel column chromatography (NH, solvent gradient; 3→50% ethyl acetate/hexane) to give 2-(4-(bis(4-methoxybenzyl)amino)-2,6-difluorophenyl)-2-methylpropan-1-ol (1.310 g, 2.97 mmol, 64.2%) as a colorless oil.

Workup

  1. stirringat 0° C., and the mixture was stirred at 0° C. for 1.5 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 3→50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-62ba9375d8344f6481d39178728e9ce5
Source dataset
uspto-grants-2016_06
Patent number
US09365520B2

Reaction notes

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