HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1366372Generated: October 31, 2026
Triphenylphosphine → (r)-1-(Benzyloxy)-3-(cyclopentylmethyl)azetidin-2-one
https://huagongshe.com/reaction/1366372
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Diisopropyl diazene-1,2-dicarboxylate | HCID 75555 | — |
| Reactant | (2R)-3-cyclopentyl-2-(hydroxymethyl)-N-[(phenylmethyl)oxy]propanamide | HCID 54467653 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (r)-1-(Benzyloxy)-3-(cyclopentylmethyl)azetidin-2-one | HCID 53718234 | 81% |
Reaction Steps
To a mixture of (2R)-3-cyclopentyl-2-(hydroxymethyl)-N-[(phenylmethyl)oxy]propanamide (22.5 g, 81 mmol) and triphenylphosphine (22.5 g, 97 mmol) in THF (800 mL) at 0° C. was added dropwise diisopropyl azodicarboxylate (18.9 mL, 97 mmol). The reaction mixture was maintained at 0° C. for 45 min and was then evaporated. Purification by chromatography on silica gel using an eluting system of hexane/EtOAc (95:5) provided (3R)-3-(cyclopentylmethyl)-1-[(phenylmethyl)oxy]-2-azetidinone (16.9 g, 81%). LCMS: (M+H)+: 260.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07893056B2 |
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| Source dataset | uspto-grants-2011_02 |
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| ORD ID | ord-ba60cc7b25ae4b8dba3f754a99ddf88a |
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| Source note | uspto-grants-2011_02 |
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