Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Acetyl chloride | HCID 6367 | — |
| Reactant | HCID 89815629 | HCID 89815629 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 89813562 | HCID 89813562 | 98.8% |
Reaction Steps
A solution of tert-butyl 5-(2-bromo-4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (2.73 g, 5.98 mmol) in 12 mL THF was treated with methanol (2.421 ml, 59.8 mmol) and was cooled to 0° C. Acetyl chloride (4.25 ml, 59.8 mmol) was added, and the reaction mixture was allowed to stir overnight. LC/MS showed mostly product, so the reaction mixture was concentrated yielding 5-(2-bromo-4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (2.32 g, 5.91 mmol). [M+H]+=357.9.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09051311B2 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-a40b1331a36b48e98c9f85465cd91af1 |
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| Source note | uspto-grants-2015_06 |
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