HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphosgene → 3-[(S)-1-(4-Trifluoromethoxy-phenyl)-ethyl]-1-oxa-3-aza-spiro[5.5]undecane-2,9-dione
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphosgene | HCID 94429 | — |
| Reactant | 3,3-Dimethyl-9-{2-[(S)-1-(4-trifluoromethoxy-phenyl)-ethylamino]-ethyl}-1,5-dioxa-spiro[5.5]undecan-9-ol | HCID 67996290 | — |
| Reactant | 12,12-dimethyl-3-[(S)-1-(4-trifluoromethoxy-phenyl)-ethyl]-1,10,14-trioxa-3-aza-dispiro[5.2.5.2]hexadecan-2-one | HCID 70498330 | — |
| Product | 3-[(S)-1-(4-Trifluoromethoxy-phenyl)-ethyl]-1-oxa-3-aza-spiro[5.5]undecane-2,9-dione | HCID 67996484 | — |
Reaction Steps
The title compound is prepared from 3,3-dimethyl-9-{2-[(S)-1-(4-trifluoromethoxy-phenyl)-ethylamino]-ethyl}-1,5-dioxa-spiro[5.5]undecan-9-ol and triphosgene following a procedure analogous to that described in Step 4 of Intermediate 2; the crude product, a mixture of the title compound and 12,12-dimethyl-3-[(S)-1-(4-trifluoromethoxy-phenyl)-ethyl]-1,10,14-trioxa-3-aza-dispiro[5.2.5.2]hexadecan-2-one, obtained after that is treated as described in Step 10 of Intermediate 2 to convert the intermediate to the title compound as well. Yield: 57% of theory; LC (method 6): tR=1.33 min; Mass spectrum (ESI+): m/z=372 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08765744B2 |
| Source dataset | uspto-grants-2014_07 |
| ORD ID | ord-fde85fdf83b4476aaae2a91d47a03bfa |
| Source note | uspto-grants-2014_07 |