Sodium hydride → Tert-butyl 3-bromo-2-oxo-1,4'-bipiperidine-1'carboxylate

HRID 407895Notes

Reaction equation

HRID 407895 reaction equation
[Br:1][CH:2]([CH2:19][CH2:20][CH2:21]Br)[C:3]([NH:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)=[O:4].[H-].[Na+]>CN(C=O)C>[Br:1][CH:2]1[CH2:19][CH2:20][CH2:21][N:5]([CH:6]2[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]2)[C:3]1=[O:4]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 67469892Tert-butyl 4-(2,5-dibromopentanamido)piperidine-1-carboxylate

Product 1

HCID 86688083Tert-butyl 3-bromo-2-oxo-1,4'-bipiperidine-1'carboxylateYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl 4-(2,5-dibromopentanamido)piperidine-1-carboxylate (2.21 g, 5.00 mmol) dissolved in DMF (10 mL) was added 60% sodium hydride (0.220 g, 5.5 mmol). The reaction was allowed to stir for 2 hours and then concentrated under vacuum. The resulting material was diluted with water and EtOAc. The organic layer was separated and the aqueous layer washed with EtOAc. The combined organic layers were dried with MgSO4 and concentrated. The residue was purified over silica gel (2:1 hexanes:EtOAc) to give tert-butyl 3-bromo-2-oxo-1,4′-bipiperidine-1′carboxylate (1.35 g, 75%) as a white solid.

Workup

  1. concentrationconcentrated under vacuum
  2. additionThe resulting material was diluted with water and EtOAc
  3. customThe organic layer was separated
  4. washthe aqueous layer washed with EtOAc
  5. dry with materialThe combined organic layers were dried with MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified over silica gel (2:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-1b18eb7582fa4a929373e9c415b63740
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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