HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 130529Generated: October 25, 2026
Citric Acid → (S)-4-(3-Hydroxy-2-methyl-propyl)-1-((S)-1-phenyl-ethyl)-pyrrolidin-2-one
https://huagongshe.com/reaction/130529
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Citric Acid | HCID 311 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | 2-Methyl-3-[(S)-5-oxo-1-((S)-1-phenyl-ethyl)-pyrrolidin-3-yl]-propionic Acid Methyl Ester | HCID 59094038 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | (S)-4-(3-Hydroxy-2-methyl-propyl)-1-((S)-1-phenyl-ethyl)-pyrrolidin-2-one | HCID 59093973 | 59% |
Reaction Steps
To the ester 93 (4.82 g, 0.017 mol) in EtOH (100 mL) was added NaBH4 (3.7 g, 0.10 mol) and the mixture heated to reflux for 2.5 hours. The solution was cooled to 0° C. and 1 M citric acid carefully added followed by water. The solution was concentrated to half volume added and extracted with ether. The combined organic extracts were dried (MgSO4) and concentrated. Flash chromatography (1:1 hexane/acetone) of the residue gave the product as an oil (2.6 g, 59%). MS m/z 262 (M+H, 100%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07381747B2 |
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| Source dataset | uspto-grants-2008_06 |
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| ORD ID | ord-3eaca8d1578647b2b6043e6e5ef5d3b7 |
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| Source note | uspto-grants-2008_06 |
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