Ethanol → Ethyl trans-4-azido-3-hydroxy-1-piperidinecarboxylate

HRID 981296Notes

Reaction equation

HRID 981296 reaction equation
[CH:1]12[O:7][CH:6]1[CH2:5][CH2:4][N:3]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:2]2.C(O)C.[N-:16]=[N+:17]=[N-:18].[Na+]>O>[N:16]([C@@H:6]1[CH2:5][CH2:4][N:3]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:2][C@H:1]1[OH:7])=[N+:17]=[N-:18].[N:16]([C@H:1]1[C@H:6]([OH:7])[CH2:5][CH2:4][N:3]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:2]1)=[N+:17]=[N-:18]

Participants

6

Reactant 3

HCID 702EthanolHCID 33557Sodium AzideHCID 12414163Ethyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate

Product 2

HCID 13677846Ethyl trans-4-azido-3-hydroxy-1-piperidinecarboxylateYield 80%HCID 86744575Ethyl trans-3-azido-4-hydroxy-1-piperidinecarboxylateYield 15%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred emulsion of 53.8 parts of ethyl 7-oxa-3-azabicyclo-[4.1,0]heptane-3-carboxylate, 17.6 parts of ethanol and 195 parts of water were added portionwise, during a 15 minutes-period, 28.6 parts of sodium azide while cooling in an ice bath. The mixture was warmed slowly to room temperature and stirring was continued overnight at room temperature. The aqueous phase was separated and extracted twice with dichloromethane. The combined organic phases were washed with a small amount of water, dried, filtered and evaporated, yielding 56.3 parts (82%) of a mixture of 80% of ethyl trans- 4-azido-3-hydroxy-1-piperidinecarboxylate (interm. 3) and 15% of ethyl trans-3-azido-4-hydroxy-1-piperidinecarboxylate.

Workup

  1. temperaturewhile cooling in an ice bath
  2. customThe aqueous phase was separated
  3. extractionextracted twice with dichloromethane
  4. washThe combined organic phases were washed with a small amount of water
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-3b854a9f83a546ed92745f920b3d07bf
Source dataset
uspto-grants-1991_02
Patent number
US04990521

Reaction notes

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