Potassium Carbonate → rac-(3R,4R)-4-azidopyrrolidin-3-ol

HRID 338987Notes

Reaction equation

HRID 338987 reaction equation
[N:1]([C@H:4]1[C@H:8]([OH:9])[CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5]1)=[N+:2]=[N-:3].C(=O)([O-])[O-].[K+].[K+]>C(O)(C(F)(F)F)=O.ClCCl.CO.ClCCl>[N:1]([C@@H:4]1[CH2:5][NH:6][CH2:7][C@H:8]1[OH:9])=[N+:2]=[N-:3]

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 15855750Tert-butyl (3R,4R)-3-azido-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 86707496rac-(3R,4R)-4-azidopyrrolidin-3-ol

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

(3R,4R)-tert-butyl 3-azido-4-hydroxypyrrolidine-1-carboxylate (3.6 g, 16.0 mmol) was stirred in 10% TFA in dichloromethane (100 mL) for 2 hours. The mixture was concentrated under reduced pressure and the residue obtained dissolved in a 10% MeOH/dichloromethane solution (50 mL) and treated with potassium carbonate (20 g) and the suspension stirred at ambient temperature for 2 hours, then filtered through a pad of Celite and washed with 10% MeOH: dichloromethane. The filtrate was concentrated to afford (3R,4R)-4-azidopyrrolidin-3-ol in quantitative yield.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue obtained
  3. filtrationfiltered through a pad of Celite
  4. washwashed with 10% MeOH
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-3edd341571604d6d8e49867405e735a2
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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