HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → (2R, 3S, 5S)-6-oxo-2,3-diphenyl-5-(3-cyclobutylbenzyl)morpholine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | tert-butyl (2R, 3S, 5S)-6-oxo-2,3-diphenyl-5-(3-cyclobutylbenzyl)-4-morpholinecaboxylate | HCID 57135938 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (2R, 3S, 5S)-6-oxo-2,3-diphenyl-5-(3-cyclobutylbenzyl)morpholine | HCID 57005921 | 91% |
Reaction Steps
According to example 82, 1.87 g of tert-butyl (2R, 3S, 5S)-6-oxo-2,3-diphenyl-5-(3-cyclobutylbenzyl)-4-morpholinecaboxylate was treated with 3.1 mL of TFA in 30 mL of CH2Cl2 for 4 h. Neutralization with 8 mL of Et3N and work-up in the usual manner gave a light yellow residue. Purification of the crude material by flash chromatography on 85 g of silica gel (8:2 hexane:EtOAc) afforded 1.35 g (91%) of (2R, 3S, 5S)-6-oxo-2,3-diphenyl-5-(3-cyclobutylbenzyl)morpholine as a thick, transparent semi-solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06319702B1 |
| Source dataset | uspto-grants-2001_11 |
| ORD ID | ord-8e29fbed559248a6b0fcc223dc02e626 |
| Source note | uspto-grants-2001_11 |