Hydroxyamine hydrochloride → (R)-3-(Benzyloxycarbonylamino)-N-hydroxy-pyrrolidine

HRID 985715Notes

Reaction equation

HRID 985715 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([CH2:19][CH2:20]OS(C)(=O)=O)[CH2:13]OS(C)(=O)=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:27][OH:28].C([O-])(O)=O.[Na+]>CCN(CC)CC.CS(C)=O.Cl>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[CH2:19][CH2:20][N:27]([OH:28])[CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 59556122(R)-2-(((Benzyloxy)carbonyl)amino)butane-1,4-diyl dimethanesulfonate

Product 1

HCID 11651598(R)-3-(Benzyloxycarbonylamino)-N-hydroxy-pyrrolidineYield 85%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 86583882DMSO triethylamineSolvent

Conditions

Temperature
60 °C

Procedure

(R)-2-(Benzyloxycarbonylamino)-1,4-dimethanesulfonyloxybutane (2.0 g; 5.06 mmol) was dissolved in a Et3N/DMSO mixture (1:1, 20 ml). Hydroxylamine hydrochloride (1.4 g; 20.2 mmol) was added and the mixture was heated at 60° C. over night. The mixture was poured in aqueous HCl (the pH was adjusted to pH=6 with NaHCO3) and extracted twice with AcOEt. The organic phase was washed with water and dried over Na2SO4. The solids were filtered off and the solvent was removed. A light yellow oil (1.4 g, purity 73%) was obtained (yield: 85%). The crude title compound was used as is.

Workup

  1. extractionextracted twice with AcOEt
  2. washThe organic phase was washed with water
  3. dry with materialdried over Na2SO4
  4. filtrationThe solids were filtered off
  5. customthe solvent was removed
  6. customA light yellow oil (1.4 g, purity 73%) was obtained (yield: 85%)

Sources & evidence

ORD record
ord-53685a3d375f454a8d31ffa4cd1b7c7a
Source dataset
uspto-grants-2005_03
Patent number
US06872836B2

Reaction notes

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