Trifluoroacetic acid → (5-Piperidin-4-yl-thiophen-3-yl)-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]oct-6-yl)-methanone

HRID 1809107Notes

Reaction equation

HRID 1809107 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[S:15][CH:16]=[C:17]([C:19]([N:21]3[CH2:27][C:26]4([CH3:29])[CH2:28][CH:22]3[CH2:23][C:24]([CH3:31])([CH3:30])[CH2:25]4)=[O:20])[CH:18]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:8]1[CH2:13][CH2:12][CH:11]([C:14]2[S:15][CH:16]=[C:17]([C:19]([N:21]3[CH2:27][C:26]4([CH3:29])[CH2:28][CH:22]3[CH2:23][C:24]([CH3:31])([CH3:30])[CH2:25]4)=[O:20])[CH:18]=2)[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 595425534-[4-(1,3,3-Trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-thiophen-2-yl]-piperidine-1 carboxylic acid tert-butyl ester

Product 1

HCID 42645767(5-Piperidin-4-yl-thiophen-3-yl)-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]oct-6-yl)-methanoneYield 81.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[4-(1,3,3-Trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-thiophen-2-yl]-piperidine-1 carboxylic acid tert-butyl ester [Enantiomer E] (0.06 g) was dissolved in DCM (2 mL) and TFA (1 mL) and the reaction stirred at room temperature for 2 hours. The solvent was evaporated and the residue product was purified by flash chromatography on a SCX-2 cartridge, washing with acetonitrile and then eluting with 2 M ammonia in methanol. The fractions containing the desired product were concentrated under vacuum to give the title compound (0.038 g). LCMS m/z 347.17 [M+H]+ RT=6.63 min (Analytical Method 2).

Workup

  1. customThe solvent was evaporated
  2. customthe residue product was purified by flash chromatography on a SCX-2 cartridge
  3. washwashing with acetonitrile
  4. washeluting with 2 M ammonia in methanol
  5. additionThe fractions containing the desired product
  6. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-51838febab75426b81789f01f125eac5
Source dataset
uspto-grants-2013_01
Patent number
US08362008B2

Reaction notes

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