Sodium hydride → HCID 67194178, compound

HRID 515363Notes

Reaction equation

HRID 515363 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]([CH:18]=[CH:19][CH:20]=1)[CH2:9]P(=O)(OCC)OCC)([O-:5])=[O:4].O=[C:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]1>O1CCCC1>[N+:3]([C:6]1[CH:7]=[C:8]([CH:18]=[CH:19][CH:20]=1)[CH:9]=[C:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]1)([O-:5])=[O:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 13675396Diethyl 3-Nitrobenzylphosphonate

Product 1

HCID 67194178HCID 67194178, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of sodium hydride (10.98 mmol, 0.439 g) in tetrahydrofuran (40 mL) was added to a stirred solution of diethyl 3-nitrobenzylphosphonate (7.32 mmol, 2 g) in tetrahydrofuran (40 mL) at 0° C. and the reaction stirred for 30 minutes. tert-Butyl 4-oxopiperidine-1-carboxylate (7.32 mmol, 1.459 g) was added and the reaction mixture stirred at room temperature overnight. The reaction mixture was concentrated under vacuum and the residue partitioned between dichloromethane and water. The organic layer was separated, dried and concentrated under vacuum. The residue was purified by silica column chromatography (eluent: 0-2% methanol in dichloromethane) to afford the intermediate tert-butyl 4-(3-nitrobenzylidene)-piperidine-1-carboxylate (2 g).

Workup

  1. stirringthe reaction mixture stirred at room temperature overnight
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. customthe residue partitioned between dichloromethane and water
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by silica column chromatography (eluent: 0-2% methanol in dichloromethane)

Sources & evidence

ORD record
ord-a14bae850ae94b83b168e5dc37ffa3db
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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