HuagongsheHuagongshe Chemistry Print Report · For research reference only
tert-butyl (2R,3S)-6-oxo-2,3-diphenylmorpholine-4-carboxylate → tert-butyl (2R,3S,5S)-6-oxo-2,3-diphenyl-5-(3-(3-pentyl)benzyl)4-morpholinecarboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | tert-butyl (2R,3S)-6-oxo-2,3-diphenylmorpholine-4-carboxylate | HCID 981230 | — |
| Reactant | Sodium bis(trimethylsilyl)amide | HCID 2724254 | — |
| Reactant | HCID 54104700 | HCID 54104700 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | tert-butyl (2R,3S,5S)-6-oxo-2,3-diphenyl-5-(3-(3-pentyl)benzyl)4-morpholinecarboxylate | HCID 57256884 | 48% |
Reaction Steps
According to example 142, 3.27 g of tert-butyl (2R, 3S)-(−)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate was alkylated with 2.23 g of 3-(3-pentyl)benzyl bromide in 70 mL of anhydrous TBF using 9.71 mL of 1 M sodium bis(trimethylsilyl)amide in THF. The crude product was subjected to flash chromatography on silica gel (9:1 hexane:EtOAc) and then recrystallization from EtOH-water to afford 2.26 g (48%) of tert-butyl (2R,3S,5S)-6-oxo-2,3-diphenyl-5-(3-(3-pentyl)benzyl)4-morpholinecarboxylate as a white crystalline solid, m.p. 143-144° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06319702B1 |
| Source dataset | uspto-grants-2001_11 |
| ORD ID | ord-883e7379d6ae44e8a3da43f6c082500b |
| Source note | uspto-grants-2001_11 |