Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetone | HCID 180 | — |
| Reactant | Iodine | HCID 807 | — |
| Reactant | Methanesulfonic Acid | HCID 6395 | — |
| Reactant | 1-(Diphenylmethyl)azetidin-3-yl methanesulfonate | HCID 2758716 | — |
| Catalyst | Palladium hydrate | HCID 23219155 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Chloroform ethylacetate | HCID 21584013 | — |
| Product | HCID 86736791 | HCID 86736791 | — |
Reaction Steps
Hydrogenate a mixture of 1.0 mole 1-benzhydryl-3-methanesulfonyloxyazetidine, 1.0 mole methanesulfonic acid and 20% palladium hydroxide-on-carbon in ethyl alcohol at ca. 60 psi until the reaction is complete as shown by absence of the Compound IV using thin layer chromatography. (Silica gel GF plates are developed in chloroform:ethyl acetate (9:1) and visualized using iodine). Add additional 20% palladium hydroxide-on-carbon and acetone and continue the hydrogenation at ca. 60 psi for 5 days. Remove the catalyst by filtration and wash with ethanol. Remove the ethanol from the combined filtrates and washes by distillation at about 40° C. under reduced pressure and wash the residue with diethyl ether and air-dry to afford 1-isopropyl-3-methanesulfonyloxyazetidine methanesulfonate.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US04183923 |
|---|
| Source dataset | uspto-grants-1980_01 |
|---|
| ORD ID | ord-9f8fcd7c27e14849919ff35f9c25f5db |
|---|
| Source note | uspto-grants-1980_01 |
|---|