Water → HCID 178516075, compound

HRID 1173826Notes

Reaction equation

HRID 1173826 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][N:3]1[C@@H:8]1[CH2:13][CH2:12][C@H:11]([O:14]C(=O)C2C=CC([N+]([O-])=O)=CC=2)[CH2:10][CH2:9]1.O.C([O-])([O-])=O.[K+].[K+]>CO>[OH:14][C@@H:11]1[CH2:10][CH2:9][C@H:8]([N:3]2[CH2:4][CH2:5][CH2:6][CH2:7][C:2]2=[O:1])[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 178525741HCID 178525741, compound

Product 1

HCID 178516075HCID 178516075, compoundYield 211.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve cis-4-nitro-benzoic acid-4-(2-oxo-piperidin-1-yl)-cyclohexyl-ester (5.0 g, 14.4 mmol) in methanol (150 mL), add water (20 mL), K2CO3 (8.7 g, 0.06 mol) and stir the reaction mixture at room temperature for 18 hours. Extract the reaction mixture with DCM (2×100 mL), dry the organic layer over Na2SO4 and remove the solvent to obtain cis-1-(4-hydroxy-cyclohexyl)-piperidin-2-one as clear oil (6.0 g). Combine cis-1-(4-hydroxy-cyclohexyl)-piperidin-2-one (6.0 g, 0.03 mol), imidazole (3.1 g, 0.05 mol), tert-butyl chloro dimethyl silane (6.9 g, 0.05 mol) and stir at room temperature for 18 hours. Wash the reaction mixture with water (150 mL) and dry the organic layer over Na2SO4. Remove the solvent and purify the residue by chromatography over silica gel (eluting with 0 to 50% EtOAc in hexane) to obtain the title compound as a clear oil (3.4 g, 76%): MS (ES+) m/z=312 (M+H)+.

Workup

  1. extractionExtract the reaction mixture with DCM (2×100 mL)
  2. dry with materialdry the organic layer over Na2SO4
  3. customremove the solvent

Sources & evidence

ORD record
ord-5422ca26e1ae424097975a2d240a9c3d
Source dataset
uspto-grants-2010_11
Patent number
US07834194B2

Reaction notes

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