Sodium hydride → HCID 86690259, compound

HRID 80799Notes

Reaction equation

HRID 80799 reaction equation
[H-].[Na+].[C:3]1([C@@H:9]([N:11]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:12][CH2:13][C:14]([O:16]CC)=O)[CH3:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C1COCC1.O.CCOC(C)=O>[O:16]=[C:14]1[CH2:13][CH2:12][N:11]([C@H:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:10])[CH2:19][C@@H:20]1[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

6

Reactant 2

HCID 24758Sodium hydrideHCID 89685893HCID 89685893, compound

Product 1

HCID 86690259HCID 86690259, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A suspension of NaH (2.24 g, 93.4 mmol) in THF (20 mL) was cooled to 0° C. and as solution of (S)-diethyl 3,3′-((1-phenylethyl)azanediyl)dipropanoate (15 g, 46.7 mmol) in THF was then added dropwise. The reaction mixture was allowed to warm to rt and then warmed to 60° C. and heated for 3 h. The mixture was diluted with water and EtOAc and the organic layer was then separated, dried (Na2SO4), filtered and concentrated. The residue was purified by FCC (5-7% EtOAc/hexanes) to give (5)-ethyl 4-oxo-1-((S)-1-phenylethyl)piperidine-3-carboxylate.

Workup

  1. additionwas then added dropwise
  2. temperaturewarmed to 60° C.
  3. temperatureheated for 3 h
  4. customthe organic layer was then separated
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by FCC (5-7% EtOAc/hexanes)

Sources & evidence

ORD record
ord-18bedf1fbcd648db8765431cae95b97d
Source dataset
uspto-grants-2014_09
Patent number
US08846656B2

Reaction notes

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