HuagongsheHuagongshe Chemistry Print Report · For research reference only
Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 59611709, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- | HCID 18462 | — |
| Reactant | 3R-hydroxymyristic acid methyl ester | HCID 9834945 | — |
| Reactant | 4-Methoxybenzyl 2,2,2-Trichloroacetimidate | HCID 11087263 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 59611709 | HCID 59611709 | 82.1% |
Reaction Steps
To a solution of compound 30 (3.50 g, 12.9 mmol) and 4-methoxybenzyl trichloroacetimidate (4.65 g, 17.3 mmol) in DCM (100 mL) was added camphorsulfonic acid (450 mg, 1.92 mmol). The mixture was stirred overnight at room temperature. The mixture was washed with a saturated solution of NaHCO3 (300 mL) and water (300 mL) and dried over Na2SO4. The drying agent was removed by filtration and the solvents removed using a rotary evaporator. The residue was purified by chromatography on silica gel (120 g RediSep column, eluting with a gradient of 0% through 30% ethyl acetate/hexanes over 70 min, 85 mL/min) to give the product 32 (4.01 g, 81%) as a colorless liquid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08722064B2 |
| Source dataset | uspto-grants-2014_05 |
| ORD ID | ord-b1f664fa6258452b8d3905e75d325426 |
| Source note | uspto-grants-2014_05 |