Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | HCID 69016586 | HCID 69016586 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 86615373 | HCID 86615373 | 97.7% |
Reaction Steps
Dissolve the tert-butyl 5-bromo-3(R)-(hydroxymethyl)-8-methoxy-3,4-dihydroisoquinoline-2(1H)-carboxylate (710 mg, 0.0019 mol) in dimethylsulfoxide (2.00 mL) and cool to 0° C. Add triethylamine (1.06 mL, 0.00763 mol) and sulfur trioxide-pyridine complex (0.607 g, 0.00381 mol). Warm to room temperature over one hour. Dilute diethyl ether (100 mL) and extract (3×25 mL) with 5% aqueous citric acid, (1×25 mL) saturated aqueous sodium chloride, and dry over magnesium sulfate. Concentrate the filtrate to give the desired product (687 mg, 94%) as an off-white semi-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-d67e986668a948d08375edce7c4de9c4 |
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| Source note | uspto-grants-2009_11 |
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