HuagongsheHuagongshe Chemistry Print Report · For research reference only
3,3-Dimethyl-1-butyne → 3-tert-butoxycarbonyl-6-(3,3-dimethyl-but-1-ynyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3,3-Dimethyl-1-butyne | HCID 13512 | — |
| Reactant | 1,1-Dimethylethyl 6-{[(trifluoromethyl)sulfonyl]oxy}-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate | HCID 57505879 | — |
| Product | 3-tert-butoxycarbonyl-6-(3,3-dimethyl-but-1-ynyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine | HCID 66706401 | 74% |
Reaction Steps
Use a method similar to the General Procedure 3 to couple 3-tert-butoxycarbonyl-6-trifluoromethanesulfonyloxy-2,3,4,5-tetrahydro-1H-benzo[d]azepine (0.5 g, 1.3 mmol) with 3,3-dimethyl-1-butyne (0.311 mL, 2.5 mmol). Purify by chromatography on silica gel eluting with hexane/EtOAc (10:1) to give 3-tert-butoxycarbonyl-6-(3,3-dimethyl-but-1-ynyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine as a yellow oil (304 mg, 74%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08580780B2 |
| Source dataset | uspto-grants-2013_11 |
| ORD ID | ord-bb795f100ad94ae39082711878a65107 |
| Source note | uspto-grants-2013_11 |