Water → HCID 13677845, compound

HRID 1948366Notes

Reaction equation

HRID 1948366 reaction equation
Br[CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH:3]1[OH:13].[N-:14]=[N+:15]=[N-:16].[Na+].O>CN(C=O)C.C1OCCOCCOCCOCCOCCOC1>[N:14]([CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH:3]1[OH:13])=[N+:15]=[N-:16]

Participants

6

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 12414165HCID 12414165, compound

Product 1

HCID 13677845HCID 13677845, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Ethyl 4-bromo-3-hydroxypiperidine-1-carboxylate (Preparation: Izamanishi, T. et al; 1982, Chem. Pharm. Bull., 30: 3617-3623) (5.1 g) was dissolved in anhydrous DMF (20 mL) under an argon atmosphere, followed by the addition of 18-crown-6 (0.27 g) and sodium azide (2.89 g). The reaction was heated at 90° C. for twenty-three hours, then stirred overnight, slowly cooling to room temperature. The reaction was then added to deionised water (150 mL) to quench it, saturated with solid sodium chloride, and extracted with EtOAc (2×200 mL). The combined EtOAc layers were washed with brine (100 mL), dried over anhydrous MgSO4 and concentrated in vacuo, yielding the title compound (4.3 g, 100%). MS (GC-EI)[(M-N2)+]: 186 for C8H14BrN4O3.

Workup

  1. temperatureslowly cooling to room temperature
  2. customto quench it
  3. extractionsaturated with solid sodium chloride, and extracted with EtOAc (2×200 mL)
  4. washThe combined EtOAc layers were washed with brine (100 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6ef22dda261640d0b49346d18a7b669e
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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