Trifluoroacetic acid → HCID 68310294, compound

HRID 1021310Notes

Reaction equation

HRID 1021310 reaction equation
[Si]([O:8][CH2:9][C:10]1[C:11]([F:33])=[C:12]([N:16]2[CH2:19][CH:18]([CH:20]3[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]3)[CH2:17]2)[CH:13]=[CH:14][CH:15]=1)(C(C)(C)C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[F:33][C:11]1[C:12]([N:16]2[CH2:19][CH:18]([CH:20]3[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]3)[CH2:17]2)=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:9][OH:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86686245HCID 86686245, compound

Product 1

HCID 68310294HCID 68310294, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-{1-[3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-fluorophenyl]azetidin-3-yl}piperidine-1-carboxylate (2.9 g) and dichloromethane (29 ml) were mixed, and TFA (7.3 ml) was added thereto, followed by stirring at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure, and CHCl3 and a saturated aqueous sodium hydrogen carbonate solution were added thereto. The aqueous layer was concentrated under reduced pressure, and CHCl3 was added to the residue, followed by stirring and filtrating. The filtrate was dried over Na2SO4 and then concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (CHCl3/MeOH) to obtain {2-fluoro-3-[3-(piperidin-4-yl)azetidin-1-yl]phenyl}methanol (1.25 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and CHCl3
  2. additiona saturated aqueous sodium hydrogen carbonate solution were added
  3. concentrationThe aqueous layer was concentrated under reduced pressure, and CHCl3
  4. additionwas added to the residue
  5. stirringby stirring
  6. filtrationfiltrating
  7. dry with materialThe filtrate was dried over Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was purified by basic silica gel column chromatography (CHCl3/MeOH)

Sources & evidence

ORD record
ord-638fe91cf00c4c40beb4c6b9c1dbba55
Source dataset
uspto-grants-2014_05
Patent number
US08716470B2

Reaction notes

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