HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tert-butyldicarbonate → Ethyl 6'-bromo-1'-(1,1-dimethylethylsulfinamido)-4-methoxy-1',3'-dihydrospiro[cyclohexane-1,2'-indene]-1'-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tert-butyldicarbonate | HCID 22064466 | — |
| Reactant | N-(6'-bromo-1'-(1-ethoxyvinyl)-4-methoxy-1',3'-dihydrospiro[cyclohexane-1,2'-indene]-1'-yl)-2-methylpropane-2-sulfinamide | HCID 58198087 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Ethyl 6'-bromo-1'-(1,1-dimethylethylsulfinamido)-4-methoxy-1',3'-dihydrospiro[cyclohexane-1,2'-indene]-1'-carboxylate | HCID 58197767 | 56.1% |
Reaction Steps
A mixture of compound 5 (50 mg, 0.11 mmol, 76% purity), tert-Butyl dicarbonate (48 mg, 0.22 mmol) and DMAP (27 mg, 0.22 mmol) in THF (5 mL) was stirred at ambient temperature overnight. The solvent was removed by evaporation in vacuo, the residue was purified by preparative TLC on silica gel eluting with petroleum ether:ethyl acetate=2:1 to give compound 6 (30 mg, 50%) as a white solid. LC-MS: 699-091-1B, tR=2.06 min in 3 min chromatography, MS (ESI) m/z=546.2 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09212153B2 |
| Source dataset | uspto-grants-2015_12 |
| ORD ID | ord-4c9628b5ab084f5e9a7638bf611dca21 |
| Source note | uspto-grants-2015_12 |