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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1917362Generated: November 1, 2026

Lawesson's reagent → [(1S,5S)-3-[(1R)-1-Phenylethyl]-4-thioxo-3-azabicyclo[3.3.0]oct-7-en-1-yl]carboxylic acid tert-butyl ester

https://huagongshe.com/reaction/1917362

Reaction equation

Participants

RoleNameHCIDCharge
ReactantLawesson's reagentHCID 87949—
Reactant[(1S,5S)-4-Oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]oct-7-en-1-yl]carboxylic acid tert-butyl esterHCID 67490826—
SolventTolueneHCID 1140—
Product[(1S,5S)-3-[(1R)-1-Phenylethyl]-4-thioxo-3-azabicyclo[3.3.0]oct-7-en-1-yl]carboxylic acid tert-butyl esterHCID 86664651133.3%

Reaction Conditions

Temperature80 °C

Reaction Steps

[(1S,5S)-4-Oxo-3-[(1R)-1-phenylethyl]-3-azabicyclo[3.3.0]oct-7-en-1-yl]carboxylic acid tert-butyl ester (88.0 mg, 0.27 mmol) was dissolved in toluene (8 mL). Lawesson's reagent (81.5 mg, 0.20 mmol) was added, and the mixture was stirred at 80° C. for four hours. The reaction solution was concentrated under reduced pressure, and the resulting residue was subjected to silica gel column chromatography (10% ethyl acetate/hexane) to give 91.6 mg of the title compound as a yellow oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08618094B2
Source datasetuspto-grants-2013_12
ORD IDord-c7d40dc8d0af4630a121af87fe3070f0
Source noteuspto-grants-2013_12