Hydroxyamine hydrochloride → HCID 178452026, compound

HRID 1040413Notes

Reaction equation

HRID 1040413 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 77.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R)-3-Cyano-pyrrolidine-1-carboxylic acid tert-butyl ester (1.02 g, 5.2 mmol), hydroxylamine hydrochloride (396 mg, 5.7 mmol) and NaHCO3 (487 mg, 5.8 mmol) were added to MeOH (12 mL) and the solution was heated to reflux. After 4 h, the reaction was concentrated in vacuo. The residue was partitioned between EtOAc and brine. The layers were separated and the organic layer was dried over Na2SO4, filtered and concentrated to yield 927 mg of crude (R)-3-(N-hydroxycarbamimidoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester as a yellow foam.

Workup

  1. temperaturethe solution was heated to reflux
  2. concentrationthe reaction was concentrated in vacuo
  3. customThe residue was partitioned between EtOAc and brine
  4. customThe layers were separated
  5. dry with materialthe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-748e87e2859e41a5bc939bcb0dcfc6f2
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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