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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 632565Generated: October 25, 2026

Heptane → 1-cyclopentyl N-[2-(1-{[2,4-bis(benzyloxy)-5-(prop-1-en-2-yl)phenyl]carbonyl}piperidin-4-yl)ethyl]-L-leucinate

https://huagongshe.com/reaction/632565

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHeptaneHCID 8900—
ReactantSodium triacetoxyborohydrideHCID 5049666—
ReactantL-leucine cyclopentyl ester tosylateHCID 86633653—
Reactant2-(1-{[2,4-Bis(benzyloxy)-5-(prop-1-en-2-yl)phenyl]carbonyl}piperidin-4-yl)acetaldehydeHCID 86686420—
Solvent1,1-DichloroethaneHCID 6365—
Product1-cyclopentyl N-[2-(1-{[2,4-bis(benzyloxy)-5-(prop-1-en-2-yl)phenyl]carbonyl}piperidin-4-yl)ethyl]-L-leucinateHCID 8668641975%

Reaction Steps

To a solution of Intermediate D (0.245 g, 0.5 mmol) in dichloroethane (10 mL) was added L-leucine cyclopentyl ester tosylate (0.398 g, 1.07 mmol) and sodium triacetoxyborohydride (0.417 g, 1.97 mmol). The mixture was stirred for one hour then loaded directly onto a silica gel column and eluted with 7:3 ethyl acetate:heptane to yield the desired product (0.250 g, 75% yield). LC/MS: m/z 667.25 [M+H]+

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09321718B2
Source datasetuspto-grants-2016_04
ORD IDord-45f7d73041424261baf06287d757f1e0
Source noteuspto-grants-2016_04