Water → 4-({5-[(4-Fluorophenyl)carbonyl]-4,5,6,7-tetrahydro[1,3]oxazolo[5,4-c]pyridin-2-yl}methoxy)phenol

HRID 1529580Notes

Reaction equation

HRID 1529580 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][C:27]1[CH:52]=[CH:51][C:30]([O:31][CH2:32][C:33]2[O:34][C:35]3[CH2:36][N:37]([C:42]([C:44]4[CH:49]=[CH:48][C:47]([F:50])=[CH:46][CH:45]=4)=[O:43])[CH2:38][CH2:39][C:40]=3[N:41]=2)=[CH:29][CH:28]=1)(C(C)(C)C)(C)C.O>C1COCC1>[F:50][C:47]1[CH:48]=[CH:49][C:44]([C:42]([N:37]2[CH2:38][CH2:39][C:40]3[N:41]=[C:33]([CH2:32][O:31][C:30]4[CH:29]=[CH:28][C:27]([OH:26])=[CH:52][CH:51]=4)[O:34][C:35]=3[CH2:36]2)=[O:43])=[CH:45][CH:46]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 666088752-[(4-{[Tert-butyl(dimethyl)silyl]oxy}phenoxy)methyl]-5-[(4-fluorophenyl)carbonyl]-4,5,6,7-tetrahydro[1,3]oxazolo[5,4-c]pyridine

Product 1

HCID 569416354-({5-[(4-Fluorophenyl)carbonyl]-4,5,6,7-tetrahydro[1,3]oxazolo[5,4-c]pyridin-2-yl}methoxy)phenolYield 45.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1M solution of tetra-butylammonium fluoride in THF (0.54 mL, 0.54 mmol) was added to a stirred solution of 2-[(4-{[tert-butyl(dimethyl)silyl]oxy}phenoxy)methyl]-5-[(4-fluorophenyl)carbonyl]-4,5,6,7-tetrahydro[1,3]oxazolo[5,4-c]pyridine (264 mg, 0.36 mmol) in THF (2 mL). The mixture was stirred at room temperature for 16 hours. The mixture was treated with water and extracted with AcOEt. The organic layer was separated, dried (MgSO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 100/0). The desired fractions were collected and the solvents evaporated in vacuo. The product was triturated with DIPE to yield (4-({5-[(4-fluorophenyl)carbonyl]-4,5,6,7-tetrahydro[1,3]oxazolo[5,4-c]pyridin-2-yl}methoxy)phenol (60 mg, 45% yield) as a white solid. C20H17FN2O4 1H NMR (400 MHz, CDCl3) δ ppm 2.72 (br. s., 2 H), 3.69 (br. s, 2 H), 4.78 (br.s., 2 H), 5.05 (br. s., 2 H), 5.86 (br. s., 1 H), 6.74 (d, J=8.8 Hz, 2 H), 6.86 (d, J=8.8 Hz, 2 H), 7.09-7.18 (m, 2 H), 7.43-7.51 (m, 2 H).

Workup

  1. extractionextracted with AcOEt
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvents evaporated in vacuo
  6. customThe crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 100/0)
  7. customThe desired fractions were collected
  8. customthe solvents evaporated in vacuo
  9. customThe product was triturated with DIPE

Sources & evidence

ORD record
ord-86e94b8779e9411ab76942d9053b7726
Source dataset
uspto-grants-2015_07
Patent number
US09090632B2

Reaction notes

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