HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dibromoethane → (1RS,2RS,4SR)-2-dimethylaminomethyl-4-isobutoxy-(3-methylsulphanyl-phenyl)-cyclohexanol hydrochloride
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dibromoethane | HCID 7839 | — |
| Reactant | 3-Bromothioanisole | HCID 2735627 | — |
| Reactant | 2-Dimethylaminomethyl-4-isobutoxy-cyclohexanone hydrochloride | HCID 18980500 | — |
| Reactant | Chlorotrimethylsilane water | HCID 86753056 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | (1RS,2RS,4SR)-2-dimethylaminomethyl-4-isobutoxy-(3-methylsulphanyl-phenyl)-cyclohexanol hydrochloride | HCID 18980483 | 32% |
Reaction Steps
Compound (22) was reacted with 1-bromo-3-methylsulphanyl-benzene corresponding to the conditions described in Example 1. In departure from the conditions described in Example 1, ether was used as the solvent and 1,2-dibromoethane was added to the batch in order to increase the yield. The crude product obtained was purified with diisopropyl ether via a silica gel column, and was taken up in tetrahydrofuran/ether. The crystals obtained after adding trimethylchlorosilane/water were recrystallised from ethyl acetate. Compound (23) was obtained in a yield of 32% theoretical.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05801201 |
| Source dataset | uspto-grants-1998_09 |
| ORD ID | ord-677f11368ebe4dfa8730a75190011983 |
| Source note | uspto-grants-1998_09 |