Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Sulfuric Acid | HCID 1118 | — |
| Reactant | HCID 69014752 | HCID 69014752 | — |
| Product | HCID 69014232 | HCID 69014232 | 98% |
Reaction Steps
Slurry the 5-bromo-8-hydroxy-1,2,3,4-tetrahydroisoquinoline-3(R)-carboxylic acid (1.538 g, 0.005652 mol) in methanol (60 mL). Add sulfuric acid (305 uL, 0.00572 mol). Heat at 85° C. for 2.5 days. Cool the solution to room temperature and concentrate under reduced pressure to a volume of ˜5 mL. Add ethyl acetate (100 mL) and neutralize with 10% aqueous potassium carbonate. Separate the layers and extract the aqueous layer with ethyl acetate (1×100 mL). Combine the organic layers and dry over magnesium sulfate. Concentrate the filtrate to give the desired product (1.65 g, 98%) as a light pink solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07618978B2 |
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| Source dataset | uspto-grants-2009_11 |
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| ORD ID | ord-6fe6aedd285a4d4f929f0bf0668272fb |
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| Source note | uspto-grants-2009_11 |
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