HCID 178455346, compound → HCID 178515521, compound

HRID 2235307Notes

Reaction equation

HRID 2235307 reaction equation
C([Si](C)(C)[O:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([N:13]2[CH2:18][CH2:17][CH2:16][CH:15]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]4[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=4)=[CH:22][C:21]=3[Cl:32])[C:14]2=[O:33])[CH2:9][CH2:8]1)(C)(C)C>CO>[Cl:32][C:21]1[CH:22]=[C:23]([C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[CH:24]=[CH:25][C:20]=1[CH2:19][CH:15]1[CH2:16][CH2:17][CH2:18][N:13]([C@H:10]2[CH2:11][CH2:12][C@H:7]([OH:6])[CH2:8][CH2:9]2)[C:14]1=[O:33]

Participants

3

Reactant 1

HCID 178455346HCID 178455346, compound

Product 1

HCID 178515521HCID 178515521, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

Dissolve trans-1-[4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-3-(2-chloro-4-pyridine-3-yl-benzyl)-piperidin-2-one (0.2 g, 0.39 mmol) in methanol containing concentrated hydrochloric acid (5% v/v) and heat at 40° C. for 1 hour. Evaporate the solvent, dissolve the residue in DCM (10 mL) and wash with saturated aqueous NaHCO3 (5 mL). Dry the organic layer over anhydrous Na2SO4, remove the solvent and purify the residue by chromatography over silica gel eluting with EtOAc to obtain the title compound as a white solid (131.4 mg, 84%): MS (ES+) m/z=399 (M+H)+.

Workup

  1. customEvaporate the solvent
  2. dissolutiondissolve the residue in DCM (10 mL)
  3. washwash with saturated aqueous NaHCO3 (5 mL)
  4. dry with materialDry the organic layer over anhydrous Na2SO4
  5. customremove the solvent
  6. custompurify the residue by chromatography over silica gel eluting with EtOAc

Sources & evidence

ORD record
ord-fef61668d87c402fb5a267941c6f88ad
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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