t-Butylammonium fluoride → {4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2,3-difluoro-5-(hydroxymethyl)phenyl}(phenyl)methanone

HRID 245366Notes

Reaction equation

HRID 245366 reaction equation
[F-].C([NH3+])(C)(C)C.[Si]([O:24][CH2:25][C:26]1[C:27]([N:42]2[CH2:47][C@H:46]([CH3:48])[O:45][C@H:44]([CH3:49])[CH2:43]2)=[C:28]([F:41])[C:29]([F:40])=[C:30]([C:32]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:33])[CH:31]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>C1COCC1>[CH3:48][C@H:46]1[O:45][C@@H:44]([CH3:49])[CH2:43][N:42]([C:27]2[C:26]([CH2:25][OH:24])=[CH:31][C:30]([C:32]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[O:33])=[C:29]([F:40])[C:28]=2[F:41])[CH2:47]1

Participants

4

Reactant 2

HCID 21866379t-Butylammonium fluorideHCID 86658052{5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2,3-difluorophenyl}(phenyl)methanone2×

Product 1

HCID 86658053{4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2,3-difluoro-5-(hydroxymethyl)phenyl}(phenyl)methanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl ammonium fluoride (435 mg, 0.002 mmol) was added in small portions to a stirred solution of {5-({[tert-butyl(diphenyl)silyl]oxy}methyl)-4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-2,3-difluorophenyl}(phenyl)methanone (Intermediate 20, 1 g, 0.002 mmol) in anhydrous THF (10 mL) at 0° C. and stirring was continued for 1 h with warming to room temperature. The solvent was removed and the residue was purified over a silica gel chromatography column using ethyl acetate-pet. ether gradient, providing the title compound. Yield: 450 mg, (75%)

Workup

  1. customThe solvent was removed
  2. customthe residue was purified over a silica gel chromatography column

Sources & evidence

ORD record
ord-8e994c788373437a98fcbd3299748904
Source dataset
uspto-grants-2014_02
Patent number
US08658641B2

Reaction notes

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