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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 706899Generated: October 30, 2026

Benzyl Alcohol → (1R,3S)-1-(Boc-amino)-3-(Cbz-amino)cyclopentane

https://huagongshe.com/reaction/706899

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBenzyl AlcoholHCID 244—
ReactantTriethylamineHCID 8471—
ReactantP,P-Diphenylphosphinic azideHCID 199401—
Reactant(1S,3R)-3-(((tert-butoxy)carbonyl)amino)cyclopentane-1-carboxylic acidHCID 1512529—
SolventTolueneHCID 1140—
Product(1R,3S)-1-(Boc-amino)-3-(Cbz-amino)cyclopentaneHCID 69244770—

Reaction Conditions

Temperature100 °C

Reaction Steps

(1S,3R)-3-(tert-butoxycarbonylamino)cyclopentanecarboxylic acid (1.03 g), diphenylphosphoryl azide (DPPA, 1.00 mL), triethylamine (0.929 mL), and benzyl alcohol (0.931 mL) were combined in toluene (10 mL) and stirred at 100° C. for 24 hours. The solution was cooled and chromatographed on silica gel using 10% ethyl acetate/hexanes to give the pure product.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09174982B2
Source datasetuspto-grants-2015_11
ORD IDord-8109c859107b446bae7f313f33f1db1d
Source noteuspto-grants-2015_11