Hydroxyamine hydrochloride → HCID 178452026, compound

HRID 1040417Notes

Reaction equation

HRID 1040417 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([C:13]#[N:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:16][OH:17].C([O-])(O)=O.[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([C:13](=[NH:14])[NH:16][OH:17])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 7018344(R)-1-Boc-3-cyanopyrrolidine

Product 1

HCID 178452026HCID 178452026, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R)-3-Cyano-pyrrolidine-1-carboxylic acid tert-butyl ester (2.04 g, 10.4 mmol), hydroxylamine hydrochloride (0.79 g, 11.4 mmol) and NaHCO3 (0.97 g, 11.6 mmol) were added to MeOH (24 mL) and the solution was heated to reflux. After 4 h, the reaction was cooled to room temperature and filtered through a fritted funnel. The solution was concentrated in vacuo. The residue was purified by reverse phase HPLC to afford (R)-3-(N-hydroxycarbamimidoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (1.28 g, 5.58 mmol, 54%) as a yellow foam.

Workup

  1. temperaturethe solution was heated to reflux
  2. filtrationfiltered through a fritted funnel
  3. concentrationThe solution was concentrated in vacuo
  4. customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-125f458d603d429491bd21906af33107
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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