Sodium Azide → tert-butyl ((3S,4S)-4-azidotetrahydro-2H-pyran-3-yl)carbamate

Participants

Role	Name	HCID	Charge
Reactant	Sodium Azide	HCID 33557	—
Reactant	Sodium Acetate	HCID 517045	—
Reactant	D-threo-Pentitol, 1,5-anhydro-2,4-dideoxy-2-[[(1,1-dimethylethoxy)carbonyl]amino]-, 3-methanesulfonate	HCID 118036785	—
Solvent	Dimethylformamide	HCID 6228	—
Product	tert-butyl ((3S,4S)-4-azidotetrahydro-2H-pyran-3-yl)carbamate	HCID 118041477	100%

Reaction Conditions

Temperature	95 °C

Reaction Steps

(3R,4R)-3-((tert-butoxycarbonyl)amino)tetrahydro-2H-pyran-4-yl methanesulfonate (2.2 g, 7.45 mmol), sodium azide (0.968 g, 14.90 mmol) and sodium acetate (1.222 g, 14.90 mmol) were taken up in DMF (15 ml). The reaction mixture was heated to 95° C. overnight. The reaction mixture was removed from heat and 20 ml of water was added and stirred while cooling. The reaction mixture was extracted with EtOAc. The organic layers were combined and washed with water. The organics were dried and solvent removed to give tert-butyl ((3S,4S)-4-azidotetrahydro-2H-pyran-3-yl)carbamate (1.8 g, 7.43 mmol, 100% yield) as a yellow oil. MS (ES+) C10H18N4O3 requires: 242, found: 265 [M+Na]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09434700B2
Source dataset	uspto-grants-2016_09
ORD ID	ord-b686d07aa7fa4898810dfb27a3f7ac5c
Source note	uspto-grants-2016_09