Skip to main content
. 2023 Aug 18;9:e1511. doi: 10.7717/peerj-cs.1511

Table 1. An excerpt from the dataset presents five examples of input and output pairs.

Original sentence Structured format
To a solution of 3-cyano-4-((1-methylethyl)oxy)benzoic acid (200 mg) in tetrahydrofuran (THF) (10 mL) was added EDC (374 mg) and HOBt (299 mg). MAKESOLUTION with 3-cyano-4-((1-methylethyl)oxy)benzoic acid (200 mg) and tetrahydrofuran (THF) (10 mL); ADD SLN; ADD EDC (374 mg); ADD HOBt (299 mg).
The resulting orange solution was partitioned between dichloromethane (10 mL) and water (10 mL) PARTITION with dichloromethane (10 mL) and water (10 mL).
Ethanol and water are added to produce a solid which is collected by filtration. ADD Ethanol; ADD water; FILTER keep precipitate.
The solution was quenched with saturated aqueous NH4Cl and extracted with CH2Cl2. QUENCH with saturated aqueous NH4Cl; EXTRACT with CH2Cl2.
The resulting mixture was filtered and the filtrate was concentrated and the residue was purified by flash column chromatography (ethylacetate/petroleum ether gradient) to afford 1-benzyl-2-(chloromethyl)pyrrolidine. FILTER keep filtrate; CONCENTRATE; PURIFY: ethyl acetate:petroleum ether; YIELD 1-benzyl-2-(chloromethyl)pyrrolidine.