Oxalyl chloride → HCID 21906247, compound

HRID 1469396Notes

Reaction equation

HRID 1469396 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18]C(C(O)=O)[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>C(Cl)Cl.CN(C=O)C>[Cl:4][C:2]([CH:1]1[CH2:18][CH2:19][N:14]([C:12]([O:11][C:7]([CH3:9])([CH3:8])[CH3:10])=[O:13])[CH2:15][CH2:16]1)=[O:3]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid

Product 1

HCID 21906247HCID 21906247, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of oxalyl chloride (8.72 ml, 17.45 mmol) in DCM (150 ml) was added 1-(tert-butoxy-carbonyl)piperidine-4-carboxylic acid (2 g, 8.72 mmol) at 0° C. Then a few drops of DMF were added. The mixture was stirred at room temperature for 2 h, washed with NH4Cl aqueous and brine. The organic layer was separated, dried (MgSO4) and concentrated. The resulting crude product was directly used in the next step.

Workup

  1. washwashed with NH4Cl aqueous and brine
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-22ad9d1b73e146e1afeb665c8a27271d
Source dataset
uspto-grants-2015_04
Patent number
US09006268B2

Reaction notes

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