HCID 178455338, compound → HCID 178516076, compound

HRID 1173825Notes

Reaction equation

HRID 1173825 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][CH2:15][C:14]2=[O:19])[CH2:9][CH2:8]1)(C)(C)C>C(O)C>[OH:6][C@H:7]1[CH2:8][CH2:9][C@H:10]([N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]2=[O:19])[CH2:11][CH2:12]1

Participants

3

Reactant 1

HCID 178455338HCID 178455338, compound

Product 1

HCID 178516076HCID 178516076, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolve trans-1-(4-[tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-piperidin-2-one (10 g, 21.1 mmol) in ethanol containing concentrated hydrochloric acid (5% v/v, 30 mL) and stir at room temperature for 18 hours. Evaporate the solvent, take the residue up in DCM (300 mL) and wash with saturated aqueous NaHCO3 (100 mL). Dry the organic layer over anhydrous Na2SO4 and remove the solvent to obtain the desired intermediate as a clear oil (4.0 g, 95%): MS (ES+) m/z=198 (M+H)+.

Workup

  1. customEvaporate the solvent
  2. washwash with saturated aqueous NaHCO3 (100 mL)
  3. dry with materialDry the organic layer over anhydrous Na2SO4
  4. customremove the solvent

Sources & evidence

ORD record
ord-cc94abf4c7624b53a079ef314e528902
Source dataset
uspto-grants-2010_11
Patent number
US07834194B2

Reaction notes

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