HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → HCID 68816116, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | (2R,4R)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester | HCID 6951202 | — |
| Reactant | 4-Methoxybenzyl 2,2,2-Trichloroacetimidate | HCID 11087263 | — |
| Catalyst | Lanthanum tris(trifluoromethanesulfonate) | HCID 2733938 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 68816116 | HCID 68816116 | 84.2% |
Reaction Steps
Add lanthanum triflate (3.6 g, 6.16 mmol) to a solution of 2,2,2-trichloro-acetimidic acid 4-methoxybenzyl ester (52.2 g, 185 mmol) and (2R,4R)-4-hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (30.2 g, 123 mmol) in toluene (200 mL). Stir 2.5 h, add methanol and concentrate. Dissolve in 25:75 dichloromethane:hexanes, filter away the insolubles and purify filtrate (silica gel chromatography, eluting with dichloromethane/ethyl acetate mixtures) to give the title compound (37.85 g, 84%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07585885B2 |
| Source dataset | uspto-grants-2009_09 |
| ORD ID | ord-5b4d513008fa476ab107ad3badc70047 |
| Source note | uspto-grants-2009_09 |