HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 341903Generated: October 31, 2026
Hydrochloric Acid → (3R,4S)-1-(4-Fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-[4-(phenylmethoxy)phenyl]-2-azetidinone
https://huagongshe.com/reaction/341903
Participants
| Role | Name | HCID | Charge |
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| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | (R)-2-Methyl-CBS-oxazaborolidine | HCID 9838490 | — |
| Reactant | (3R,4S)-4-[4-(Benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one | HCID 10720110 | — |
| Reactant | HCID 131721059 | HCID 131721059 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (3R,4S)-1-(4-Fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-[4-(phenylmethoxy)phenyl]-2-azetidinone | HCID 10577302 | — |
Reaction Steps
Add (R)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c]-[1,3,2]oxazaborole (120 mg, 0.43 mmol) to 1-(4-fluorophenyl)-3(R)-(3-(4-fluorophenyl)-3-oxopropyl)-4(S)-(4-benzyloxyphenyl)-2-azetidinone (0.95 g, 1.91 mmol) in THF (3 mL) and cool to -20° C. After 5 min., add borohydride-dimethylsulfide complex (2M in THF, 0.85 mL, 1.7 mmol) dropwise over 0.5 h. After a total of 1.5 h, add CH3OH followed by HCl (1N) and extract the reaction mixture with EtOAc to obtain 1-(4-fluorophenyl)-3(R)-(3(S)-(4-fluorophenyl)-3-hydroxypropyl)-4(S)-(4-benzyloxyphenyl)-2-azetidinone.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05856473 |
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| Source dataset | uspto-grants-1999_01 |
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| ORD ID | ord-1f13f27e3597424995b6dff231048107 |
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| Source note | uspto-grants-1999_01 |
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