Potassium Carbonate → HCID 66750821, compound

HRID 534828Notes

Reaction equation

HRID 534828 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C([O-])([O-])=O.[K+].[K+].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[N+:40]([CH2:42][C:43]([O:45][CH3:46])=[O:44])#[C-:41]>CN(C)C=O>[CH3:46][O:45][C:43]([C:42]1[N:40]=[CH:41][O:16][C:14]=1[CH:11]1[CH2:10][CH2:9][N:8]([C:1]([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2])[CH2:13][CH2:12]1)=[O:44]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 199401P,P-Diphenylphosphinic azideHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 547815Methyl isocyanoacetate

Product 1

HCID 66750821HCID 66750821, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice-cold mixture of 1-Boc-4-piperidinecarboxylic acid (9.65 g, 42.1 mmol) and K2CO3 (23.3 g, 168.4 mmol) in N,N-dimethylformamide (60 mL) were added diphenylphosphoryl azide (16.1 g, 58.5 mmol) and methyl isocyanoacetate (5.0 g, 50.5 mmol). After being stirred at room temperature for 16 h, the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with water, saturated NaHCO3 solution, and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate 80:20 to 20:80) to give the title compound (9.07 g, 69%) as a yellow solid.

Workup

  1. customthe reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with water, saturated NaHCO3 solution, and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate 80:20 to 20:80)

Sources & evidence

ORD record
ord-a0da552a64df44acb5e21682da69c15b
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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