HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1650296Generated: October 30, 2026
Lawesson's reagent → (2S)-2-t-butyldimethylsilyloxymethyl-1-methyl-5-thioxopyrrolidine
https://huagongshe.com/reaction/1650296
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Lawesson's reagent | HCID 87949 | — |
| Reactant | (5S)-5-[(tert-butyldimethylsilyloxy)methyl]-1-methylpyrrolidin-2-one | HCID 18639170 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (2S)-2-t-butyldimethylsilyloxymethyl-1-methyl-5-thioxopyrrolidine | HCID 57091879 | 181.5% |
Reaction Steps
To a solution of (2S)-2-t-butyldimethylsilyloxymethyl 1-methyl-5-pyrrolidone (16 g) in tetrahydrofuran (160 ml) was added Lawesson's Reagent [2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide] (14.6 g) at ambient temperature. After stirring at 60° C. under nitrogen for 1 hour, the solvent was removed. The residue was chromatographed on silica gel eluting with a mixture of acetone and dichloromethane (1:9 V/V) to give (2S)-2-t-butyldimethylsilyloxymethyl-1-methyl-5-thioxopyrrolidine (17.0 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04923857 |
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| Source dataset | uspto-grants-1990_05 |
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| ORD ID | ord-24164014a8914facb78dd83063566fb0 |
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| Source note | uspto-grants-1990_05 |
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