Potassium Carbonate → HCID 86695573, compound

HRID 1465689Notes

Reaction equation

HRID 1465689 reaction equation
Cl.N1(S([N:10]=[N+:11]=[N-])(=O)=O)C=CN=C1.[NH2:13][C@@H:14]1[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]1.C([O-])([O-])=O.[K+].[K+]>CO>[N:13]([C@@H:14]1[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]1)=[N+:10]=[N-:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1501974tert-butyl (3R)-3-aminopiperidine-1-carboxylateHCID 235839821H-Imidazole-1-sulfonyl azide hydrochloride

Product 1

HCID 86695573HCID 86695573, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Imidazole-1-sulfonyl azide hydrochloride (1.03 g, 6.0 mmol) was added to (R)-tert-butyl 3-aminopiperidine-1-carboxylate (1.0 g, 5.0 mmol), K2CO3 (1.33 g, 10.0 mmol) and CuSO4.5H2O (0.012 g, 0.05 mmol) in MeOH (30 mL) and the mixture was stirred at room temperature for 12 h. The mixture was concentrated, diluted with H2O (50 mL), extracted with EtOAc (3×60 mL). The combined organic layers were dried (MgSO4), filtered and concentrated to give (R)-tert-butyl 3-azidopiperidine-1-carboxylate (0.65 g).

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with H2O (50 mL)
  3. extractionextracted with EtOAc (3×60 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c8283b2774f74b2aafbfe60944c148b8
Source dataset
uspto-grants-2015_04
Patent number
US08999966B2

Reaction notes

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