HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → Ethyl (3S, 4aR, 6S, 8aR) 6-(2-cyano-3-methyl-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 | 2-Amino-5-methylbenzonitrile | HCID 242778 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| 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-cyano-3-methyl-phenylamino)-2-methoxycarbonyl-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-3-carboxylate | HCID 131725057 | 13% |
Reaction Steps
Following the procedures from Example 3A, and using 1.076 g (3.8 mmol) of ethyl 6-oxo-2-(methoxycarbonyl)-decahydroisoquinoline-3-carboxylate, 1.36 g (10.0 mmol) of 2-amino-5-methylbenzonitrile, 0.67 mL (12 mmol) of glacial acetic acid, and 1.14 g (5.4 mmol) of sodium triacetoxyborohydride, flash chromatography (silica gel, hexane-ethyl acetate 3:1) afforded 105 mg (13% 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-5d906be7274746c586e3762f19a43525 |
| Source note | uspto-grants-2005_08 |