HuagongsheHuagongshe Chemistry Print Report · For research reference only
alpha-Bromo-o-fluorotoluene → 5(S)[1(S)-(Boc-Amino)-2-phenylethyl]-3(R)-[(o-fluorophenyl)methyl]dihydrofuran-2-(3H)-one
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
Analogously to Example 21 D) 1)c), 5.0 g (16.37 mmol) of 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]-dihydrofuran-2-(3H)-one [Example 21 D) 1)b)] dissolved in 75 ml of THF are deprotonated at -75° C. with 32.7 ml of lithium bis(trimethylsilyl)amide 1M in THF and alkylated starting at -75° C. with 2.1 ml (18.0 mmol) of o-fluorobenzyl bromide (Fluka; Buchs/Switzerland) (warming up during 60 min up to max. -60° C.). Column chromatography (SiO2, hexane/ethyl acetate 3:1) yields the title compound: TLC Rf (D)=0.61.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05643878 |
| Source dataset | uspto-grants-1997_07 |
| ORD ID | ord-902ed0c670644c62bab6deba00429105 |
| Source note | uspto-grants-1997_07 |