HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dichloromethane → 4-[5-(Cyclopropyl-amino)-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalene-2-yl-ethynyl]-2-fluoro-benzoic acid ethyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Cyclopropylamine | HCID 69828 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | 2-Fluoro-4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydronaphthalen-2-ylethynyl)benzoic acid ethyl ester | HCID 12971712 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Hexane | HCID 8058 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 4-[5-(Cyclopropyl-amino)-8,8-dimethyl-5,6,7,8-tetrahydro-naphthalene-2-yl-ethynyl]-2-fluoro-benzoic acid ethyl ester | HCID 12971713 | — |
Reaction Steps
Following general procedure G and using 2-fluoro-4-(8,8-dimethyl-5-oxo-5,6,7,8-tetrahydro-naphthalene-2-ylethynyl)-benzoic acid ethyl ester (Compound 9, 0.132 g, 0.3 mmol), dichloromethane (4 mL), acetonitrile(2 mL), cyclopropyl amine(1 mL, 14.45 mmol), acetic acid (1 mL)and sodium cyanoborohydride (0.18 g, 2.86 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 16-20% ethyl acetate in hexane as the eluent, the title compound was obtained as a pale yellow oil (0.1 g, 82%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06495552B2 |
| Source dataset | uspto-grants-2002_12 |
| ORD ID | ord-e281bdefac5e435ca5d6113fbaec788e |
| Source note | uspto-grants-2002_12 |