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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1423412Generated: October 26, 2026

Sodium Azide → tert-butyl [(1S,3S)-3-azidocyclopentyl]carbamate

https://huagongshe.com/reaction/1423412

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium AzideHCID 33557—
Reactant(1R,3S)-3-[(tert-butoxycarbonyl)amino]cyclopentyl methanesulfonateHCID 86608906—
SolventDimethylformamideHCID 6228—
Producttert-butyl [(1S,3S)-3-azidocyclopentyl]carbamateHCID 86608905—

Reaction Conditions

Temperature60 °C

Reaction Steps

Crude product from example C4 is dissolved in dry DMF (180 mL). After addition of sodium azide (11.7 g; 180.0 mmol) the reaction mixture is stirred for three days at 60° C. After filtration the reaction mixture is concentrated under reduced pressure, diluted with dichloromethane, extracted with water, half saturated brine and dried over MgSO4. After column chromatography on silica gel (cyclohexane/AcOEt—9:1) 11.8 g of the title compound is obtained as pale yellow oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08927557B2
Source datasetuspto-grants-2015_01
ORD IDord-a8bc33571efb4c0baa92323d50b35ca6
Source noteuspto-grants-2015_01