Sodium hydride → HCID 178455338, compound

HRID 2235232Notes

Reaction equation

HRID 2235232 reaction equation
[C:1]([Si:5]([CH3:22])([CH3:21])[O:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14](=[O:20])[CH2:15][CH2:16][CH2:17][CH2:18]Cl)[CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+]>C1COCC1>[C:1]([Si:5]([CH3:22])([CH3:21])[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:20])[CH2:9][CH2:8]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 178455366HCID 178455366, compound

Product 1

HCID 178455338HCID 178455338, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

Dissolve trans-5-chloro-pentanoic acid-[4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-amide (22.7 g, 65.1 mmol) in anhydrous THF (500 mL), add sodium hydride (60% dispersion in mineral oil, 13.0 g, 0.32 mol) by portions and heat the reaction mixture at 70° C. for 18 hours. Cool the reaction mixture to room temperature, quench with water (200 mL) and extract with DCM (3×100 mL). Dry the organic layer over anhydrous Na2SO4, remove the solvent and purify the residue by chromatography over silica gel (eluting with 0 to 50% EtOAc in hexane) to obtain trans-1-(4-[tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-piperidin-2-one as a white solid (15.0 g, 74%): MS (ES+) m/z=312 (M+H)+.

Workup

  1. temperatureCool the reaction mixture to room temperature
  2. customquench with water (200 mL)
  3. extractionextract with DCM (3×100 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 0 to 50% EtOAc in hexane)

Sources & evidence

ORD record
ord-a9f0eed35b29435d8b51bc88e551623f
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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