HuagongsheHuagongshe Chemistry Print Report · For research reference only
Formaldehyde → 2-((3aS,5S,6aR)-3a-(6-(trifluoromethyl)-3,4-dihydro-2H-benzo[e][1,3]oxazine-3-carbonyl)hexahydro-2H-cyclopenta[b]furan-5-yl)isoindoline-1,3-dione
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | p-Toluenesulfonic acid monohydrate | HCID 521998 | — |
| Reactant | (3aS,5S,6aR)-5-(1,3-dioxoisoindolin-2-yl)-N-(2-hydroxy-5-(trifluoromethyl)benzyl)hexahydro-2H-cyclopenta[b]furan-3a-carboxamide | HCID 86708154 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 2-((3aS,5S,6aR)-3a-(6-(trifluoromethyl)-3,4-dihydro-2H-benzo[e][1,3]oxazine-3-carbonyl)hexahydro-2H-cyclopenta[b]furan-5-yl)isoindoline-1,3-dione | HCID 86708155 | — |
Reaction Steps
A solution of the product of Step C (7.97 g, 15.5 mmol, 1 eq), paraformaldehyde (9.28 g, 310 mmol, 20 eq) and p-toluenesulfonic acid hydrate (2.94 g, 15.5 mmol, 1 eq) in toluene (300 mL) was heated to 130° C. for 18 hours in a flask equipped with a Dean-Stark trap. The solution was cooled to rt and concentrated. Purification by chromatography (200 g column) eluting with 25 to 60 to 100% ethyl acetate/heptane afforded the product of Step D. Calculated for C25H21F3N2O5: 487.1 (M+1). found: 487.2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09150532B2 |
| Source dataset | uspto-grants-2015_10 |
| ORD ID | ord-e9a8d07db17649ff8cbfc59d63bfd125 |
| Source note | uspto-grants-2015_10 |