HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → Ethyl (3S, 4aR, 6S, 8aR) 6-(2-ethoxycarbonyl-4-fluoro-phenylamino)-2-methoxycarbonyl-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Sodium | HCID 5360545 | — |
| Reactant | Ethyl 2-amino-5-fluorobenzoate | HCID 11126923 | — |
| Reactant | 3-Ethyl 2-Methyl 6-oxooctahydroisoquinoline-2,3(1H)-dicarboxylate | HCID 14877978 | — |
| Solvent | Ethyl acetate hexane | HCID 21226206 | — |
| Product | Ethyl (3S, 4aR, 6S, 8aR) 6-(2-ethoxycarbonyl-4-fluoro-phenylamino)-2-methoxycarbonyl-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate | HCID 131725055 | 22% |
Reaction Steps
Following the procedures from Example 1A, and using ethyl 6-oxo-2-(methoxycarbonyl)-decahydroisoquinoline-3-carboxylate (537 mg, 1.9 mmol), 2-amino-5-fluoro-benzoic acid ethyl ester (183 mg, 1.0 mmol), glacial acetic acid (0.36 mL, 6.0 mmol), and sodium triacethoxyborohydride (590 mg, 2.8 mmol), flash chromatography (silica gel, hexane-ethyl acetate 3:1) afforded 95 mg (22% yield) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06924294B2 |
| Source dataset | uspto-grants-2005_08 |
| ORD ID | ord-8ea732db089447bc8de90f2077c07d8b |
| Source note | uspto-grants-2005_08 |