HuagongsheHuagongshe Chemistry Print Report · For research reference only
Propargyl bromide → 2-Bromomethylnaphthalene
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Propargyl bromide | HCID 7842 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | (3S,4S)-tert-Butyl 3-hydroxy-4-(4-hydroxyphenyl)piperidine-1-carboxylate | HCID 21713087 | — |
| Solvent | Acetone | HCID 180 | — |
| Product | 2-Bromomethylnaphthalene | HCID 70320 | — |
| Product | tert-butyl (3RS,4RS)-3-hydroxy-4-(4-prop-2-ynyloxy-phenyl)-piperidine-1-carboxylate | HCID 54010348 | — |
Reaction Steps
In an analogous manner to that described in Example 44 (e), by alkylating tert-butyl (3RS,4RS)-3-hydroxy-4-(4-hydroxy-phenyl)-piperidine-1-carboxylate [Example 46 (b)] with propargyl bromide in the presence of potassium carbonate in acetone there was obtained tert-butyl (3RS,4RS)-3-hydroxy-4-(4-prop-2-ynyloxy-phenyl)-piperidine-1-carboxylate, alkylation of which with 2-bromomethylnaphthalene in analogy to Example 1 (g) gave tert-butyl (3RS,4RS)-3-(naphthalen-2-ylmethoxy)-4-(4-prop-2-ynyloxy-phenyl)-piperidine-1-carboxylate as a pale yellow solid; MS: 472 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06051712 |
| Source dataset | uspto-grants-2000_04 |
| ORD ID | ord-f20c35b7d5654a25a1efbd4f6e41a4e4 |
| Source note | uspto-grants-2000_04 |