Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1,1-Dibromoethane | HCID 11201 | — |
| Reactant | Tert-butyl 3-iodoazetidine-1-carboxylate | HCID 11000522 | — |
| Reactant | CID 71317501 | HCID 71317501 | — |
| Reactant | HCID 86706566 | HCID 86706566 | — |
| Catalyst | Zinc | HCID 23994 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 68310141 | HCID 68310141 | 30.3% |
Reaction Steps
Zinc dust (252 mg) was suspended in DMA (0.5 ml) and heated to 65° C. Subsequently, trichloromethylsilane (27 mg) and dibromoethane (34 mg) were added and the mixture was stirred at 65° C. for 30 min. Then 1-BOC-3-iodoazetidine (465 mg) in 0.5 ml of DMA was added dropwise and the mixture was stirred for a further 30 min. (R)-5-(4-bromo-2-fluorobenzyl)-2-methoxy-6,6-dimethyl-5,6-dihydro-[1,4,3]oxathiazine 4,4-dioxide (250 mg) was dissolved in 1 ml and added dropwise to the warm solution, and the mixture was stirred at 65° C. for a further 30 min. Copper(I) iodide (25 mg) and 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) chloride (53 mg) were added and the suspension was heated to 85° C. for 1 hour. After cooling, the mixture was filtered through a membrane. The solution was purified by means of preparative HPLC. This gave the product (91 mg) with a molecular weight of 456.5 g/mol (C21H29FN2O6S), MS (ESI): (M-butene+H+) 401.5 g/mol.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08809325B2 |
|---|
| Source dataset | uspto-grants-2014_08 |
|---|
| ORD ID | ord-e8bbfd22f9c74ecdac8705e5ebe6f040 |
|---|
| Source note | uspto-grants-2014_08 |
|---|
