HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1006788Generated: October 31, 2026
Triethylsilane → (3R,5S)-5-benzylsulfanylmethyl-1-methanesulfonyl-pyrrolidine-3-thiol
https://huagongshe.com/reaction/1006788
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylsilane | HCID 12052 | — |
| Reactant | (2S,4R)-2-benzylsulfanylmethyl-1-methanesulfonyl-4-(4-methoxy-benzylsulfanyl)-pyrrolidine | HCID 69430272 | — |
| Reactant | TFA triethylsilane | HCID 131722655 | — |
| Solvent | Trifluoroacetic acid | HCID 6422 | — |
| Product | (3R,5S)-5-benzylsulfanylmethyl-1-methanesulfonyl-pyrrolidine-3-thiol | HCID 86584837 | 21% |
Reaction Steps
(TFA/triethylsilane for not labile methoxy-benzylsulfanyl, Method 2): 100 mg (0.23 mmol) of (2S,4R)-2-benzylsulfanylmethyl-1-methanesulfonyl-4-(4-methoxy-benzylsulfanyl)-pyrrolidine was dissolved in 8.2 ml TFA and treated at 0° C. with 0.35 ml (2.38 mmol) triethylsilane. The reaction was warmed up over night, heated 2.5 min at 80° C. and evaporated. Flash silica gel column (CH2Cl2/EtOAc 99:1) gave 15 mg (21%) of (3R,5S)-5-benzylsulfanylmethyl-1-methanesulfonyl-pyrrolidine-3-thiol, mp 101.5-103.5° C., MS: 318 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06790860B2 |
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| Source dataset | uspto-grants-2004_09 |
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| ORD ID | ord-7406cef5646b43609d71a9e17e5518c5 |
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| Source note | uspto-grants-2004_09 |
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