HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 9H-fluoren-9-ylmethyl-9-(phenylmethyl)-1-oxa-4,9-diazaspiro[5,5]undecane-4-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 9-Fluorenylmethyl chloroformate | HCID 34367 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 9-Benzyl-1-oxa-4,9-diazaspiro[5.5]undecane | HCID 35753744 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 9H-fluoren-9-ylmethyl-9-(phenylmethyl)-1-oxa-4,9-diazaspiro[5,5]undecane-4-carboxylate | HCID 58299672 | 22.5% |
Reaction Steps
To a solution of compound 402 (2.81 g, 11.4 mmol) in 1,4-dioxane (53 mL) was added 10% sodium bicarbonate in water (21.5 mL) followed by 9-fluorenylmethyl chloroformate (2.96 g, 11.4 mmol). The resulting mixture was stirred at room temperature for four hours, and then neutralized with 3N HCl. The solution was concentrated to a solid and then purified by flash chromatography (0-10% methanol in DCM with 1% NH4OH) to give compound 403 as a white solid (1.2 g, 22.5%). LCMS-ESI (POS), M/Z, M+1: Found 469.1, Calculated 469.2.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08980903B2 |
| Source dataset | uspto-grants-2015_03 |
| ORD ID | ord-3e4f2ae7015d49cfa9d81488bc567662 |
| Source note | uspto-grants-2015_03 |