Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | 1-[(1S,3R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(3-hydroxy-3-methyl-butyl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]-2-(2-chloro-6-methoxy-phenyl)ethanone | HCID 123784459 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 117720336 | HCID 117720336 | 73.1% |
Reaction Steps
Dissolve 1-[(1S,3R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(3-hydroxy-3-methyl-butyl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]-2-(2-chloro-6-methoxy-phenyl)ethanone (0.58 g, 1.04 mmol) in THF (5.3 mL). Add acetic acid (16 mL, 279 mmol) and water (5.3 mL). Stir at 50° C. for 1.5 hours. Concentrate under reduced pressure. Dissolve the residue in ethyl acetate and wash with saturated sodium bicarbonate solution, water, and brine. Dry over sodium sulfate, filter, and concentrate under reduced pressure. Purify the residue by silica gel chromatography, eluting with acetone: hexanes (gradient, 0-30%) to give the title compound as a white foam (0.34 g, 0.76 mmol). MS (m/z): 446.0 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08962654B2 |
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| Source dataset | uspto-grants-2015_02 |
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| ORD ID | ord-73972013b1ee400d823fb98c5911a509 |
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| Source note | uspto-grants-2015_02 |
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