Toluene → HCID 68180868, compound

HRID 538687Notes

Reaction equation

HRID 538687 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([NH:11][CH:12]3[CH2:20][C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH2:13]3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.CC([O-])(C)C.[K+].C([N:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH:35]1[CH2:40][CH2:41]OS(C(F)(F)F)(=O)=O)C1C=CC=CC=1.[C:50]1([CH3:56])[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>C(OCC)(=O)C>[CH2:56]([CH:40]([CH:35]1[CH2:36][CH2:37][CH2:38][CH2:39][NH:34]1)[CH2:41][N:11]([C:9]1[CH:8]=[CH:7][C:6]2[O:1][CH2:2][CH2:3][O:4][C:5]=2[CH:10]=1)[CH:12]1[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13]1)[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1

Participants

6

Reactant 4

HCID 1140Toluene2×HCID 23665647Potassium tert-butoxideHCID 43512818HCID 43512818, compoundHCID 86669794HCID 86669794, compound2×

Product 1

HCID 68180868HCID 68180868, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of compound 57 (1 g, 3.74 mmol) in dry toluene (25 mL) was added KOtBu (0.63 g, 5.61 mmol) at 0° C. and the solution was heated at 50° C. for 5 hours. A solution of trifluoromethanesulfonic acid 2-(1-benzyl-piperidin-2-yl)-ethyl ester (58) (1.4 g, 4.11 mmol) in dry toluene (5 mL) was then added at 0° C. and refluxed for 16 hours. TLC showed incomplete conversion of the starting material, hence another 0.5 eq of compound 58 was added and refluxed for 16 hours. The reaction mixture was diluted with ethyl acetate and the organic layer was washed with water and brine. The solution was dried over anhydrous Na2SO4, filtered and concentrated. The crude material was purified by Combiflash® chromatrography eluting with 7-8% methanol-DCM to get compound 59.

Workup

  1. temperaturerefluxed for 16 hours
  2. temperaturerefluxed for 16 hours
  3. washthe organic layer was washed with water and brine
  4. dry with materialThe solution was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by Combiflash® chromatrography
  8. washeluting with 7-8% methanol-DCM

Sources & evidence

ORD record
ord-f65d9a3971b64f9bac7556f1b45943cf
Source dataset
uspto-grants-2014_10
Patent number
US08865741B2

Reaction notes

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