HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-(Bromomethyl)benzonitrile → HCID 70090413, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-(Bromomethyl)benzonitrile | HCID 86996 | — |
| 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 | HCID 70090413 | HCID 70090413 | — |
Reaction Steps
In analogy with Example 1h), 1.5 g of 5(S)-[1(S)-(Boc-amino)-2-phenylethyl]dihydrofuran-2-(3H)-one, dissolved in 32 ml of THF, are deprotonated with 9.8 ml of a 1M solution of lithium bis(trimethylsilyl)amide in THF, and alkylated with 1.0 g of 4-bromomethylbenzonitrile (Fluka; Buchs/Switzerland) dissolved in 3 ml of THF. Column chromatography (SiO2, hexane/ethyl acetate 1:1) affords the pure title compound: TLC Rf (B)=0.33.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05807891 |
| Source dataset | uspto-grants-1998_09 |
| ORD ID | ord-04ea3ce24bf44965a5e4561bb9a42565 |
| Source note | uspto-grants-1998_09 |