HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2394087Generated: October 25, 2026
alpha-Bromo-o-fluorotoluene → 5(S)[1(S)-(Boc-Amino)-2-phenylethyl]-3(R)-[(o-fluorophenyl)methyl]dihydrofuran-2-(3H)-one
https://huagongshe.com/reaction/2394087
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | alpha-Bromo-o-fluorotoluene | HCID 67968 | — |
| Reactant | Lithium Hexamethyldisilazide | HCID 2733832 | — |
| Reactant | tert-butyl(1S)-1-[(2S)-5-oxotetrahydrofuran-2-yl]-2-phenylethylcarbamate | HCID 10870461 | — |
| Reactant | Ethyl acetate hexane | HCID 21226206 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 5(S)[1(S)-(Boc-Amino)-2-phenylethyl]-3(R)-[(o-fluorophenyl)methyl]dihydrofuran-2-(3H)-one | HCID 70149348 | — |
Reaction Steps
In analogy with Example 1h), 5.0 g (16.37 mmol) of 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]dihydrofuran-2-(3H)-one [Example 2b)] dissolved in 75 ml of THF are deprotonated, at -75° C., with 32.7 ml of a 1M solution of lithium bis(trimethylsilyl)amide in THF, and alkylated with 2.1 ml (18.0 mmol) of o-fluorobenzyl bromide (Fluka; Buchs/Switzerland) at -75° C. initially (heating to a maximum of -60° C. over a period of 60 min). Column chromatography (SiO2, hexane/ethyl acetate, 3:1) affords the title compound: TLC Rf (D)=0.61.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05807891 |
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| Source dataset | uspto-grants-1998_09 |
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| ORD ID | ord-41b8553333cf4b72a5a3b66fb54cea97 |
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| Source note | uspto-grants-1998_09 |
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