Acetic Acid → HCID 59542586, compound

HRID 1809088Notes

Reaction equation

HRID 1809088 reaction equation
C([SiH2][O:6][C:7](C)(C)[C:8]1[S:12][CH:11]=[C:10]([C:13]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[O:14])[CH:9]=1)(C)(C)C.[F-].C([NH3+])(C)(C)C.C(O)(=O)C>O1CCCC1>[OH:6][CH2:7][C:8]1[S:12][CH:11]=[C:10]([C:13]([N:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2)=[O:14])[CH:9]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 21866379t-Butylammonium fluorideHCID 131730179HCID 131730179, compound

Product 1

HCID 59542586HCID 59542586, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[5-(tert-Butyl-dimethyl-silanyloxymethyl)-thiophen-3-yl]-piperidin-1-yl-methanone (0.96 g, 2.83 mmol) was dissolved in tetrahydrofuran (15 mL) and t-butylammonium fluoride (1 M in THF; 3.12 mL) and acetic acid (1 mL) were added. The reaction mixture was stirred overnight then partitioned between diethyl ether and saturated aqueous sodium hydrogen carbonate. The organic solution was separated and dried over magnesium sulphate, filtered and the solvent removed. The residue was purified by flash chromatography on silica, eluting with 30% ethyl acetate in pentane. The fractions containing the desired product were concentrated under vacuum to give the title compound as a clear oil (0.41 g). LCMS m/z 226 [M+H]+ RT=6.15 min (Analytical Method 4).

Workup

  1. customthen partitioned between diethyl ether and saturated aqueous sodium hydrogen carbonate
  2. customThe organic solution was separated
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent removed
  6. customThe residue was purified by flash chromatography on silica
  7. washeluting with 30% ethyl acetate in pentane
  8. additionThe fractions containing the desired product
  9. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-a099e4335fe24ba3a655efabfaff133f
Source dataset
uspto-grants-2013_01
Patent number
US08362008B2

Reaction notes

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