Ammonia → Benzyl 3-amino-4-hydroxypyrrolidine-1-carboxylate

HRID 400450Notes

Reaction equation

HRID 400450 reaction equation
[CH:1]12[O:6][CH:5]1[CH2:4][N:3]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[CH2:2]2.[NH3:17]>>[NH2:17][CH:1]1[CH:5]([OH:6])[CH2:4][N:3]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:2]1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 22147363Benzyl 6-oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate

Product 1

HCID 17917965Benzyl 3-amino-4-hydroxypyrrolidine-1-carboxylate

Procedure

6.5 g benzyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate in 80 mL 33% aqueous ammonia solution was stirred 20 h in a closed vessel. The reaction was cooled and extracted with dichlormethane. The organic layer was washed with sodium chloride solution and evaporated to give 6.1 g of the desired product.

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted with dichlormethane
  3. washThe organic layer was washed with sodium chloride solution
  4. customevaporated

Sources & evidence

ORD record
ord-bfdcbdea71ed4404b77bb1e35eddde82
Source dataset
uspto-grants-2014_06
Patent number
US08741892B2

Reaction notes

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