HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrogen Bromide → {(R)-1-[2-fluoro-4-(6-hydroxy-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-phenyl]-pyrrolidin-3-yl}-methyl-carbamic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrogen Bromide | HCID 260 | — |
| Reactant | Di-tert-butyl dicarbonate | HCID 90495 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | {(R)-1-[2-fluoro-4-(6-methoxy-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-phenyl]-pyrrolidin-3-yl}-methyl-carbamic acid tert-butyl ester | HCID 68989909 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | {(R)-1-[2-fluoro-4-(6-hydroxy-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-phenyl]-pyrrolidin-3-yl}-methyl-carbamic acid tert-butyl ester | HCID 68991872 | — |
Reaction Steps
According to Method L, {(R)-1-[2-fluoro-4-(6-methoxy-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-phenyl]-pyrrolidin-3-yl}-methyl-carbamic acid tert-butyl ester was treated with hydrogen bromide. The raw product (5.5 g) was dissolved in 1,4-dioxan (50 mL) and water (50 mL), sodium hydrogencarbonate (2.6 g) and lastly Boc2O (3.38 g) were added. After 3 hours the 1,4-dioxan was removed in the rotary evaporator and the residue was distributed between water and ethyl acetate. The organic phase was dried over sodium sulfate and concentrated. In this way the product was obtained with molecular weight 455.53 (C25H30FN3O4); MS (ESI): 456 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08822495B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-acb4ebd49b784df997b58c5fd71106eb |
| Source note | uspto-grants-2014_09 |