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

Participants

Role	Name	HCID	Charge
Reactant	Hydroxyamine hydrochloride	HCID 443297	—
Reactant	Sodium Bicarbonate	HCID 516892	—
Reactant	(R)-2-(((Benzyloxy)carbonyl)amino)butane-1,4-diyl dimethanesulfonate	HCID 59556122	—
Solvent	Hydrochloric Acid	HCID 313	—
Solvent	DMSO triethylamine	HCID 86583882	—
Product	(R)-3-(Benzyloxycarbonylamino)-N-hydroxy-pyrrolidine	HCID 11651598	85%

Reaction Conditions

Temperature	60 °C

Reaction Steps

(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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06872836B2
Source dataset	uspto-grants-2005_03
ORD ID	ord-53685a3d375f454a8d31ffa4cd1b7c7a
Source note	uspto-grants-2005_03