HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphosgene → 3-[(S)-1-(4-methoxy-phenyl)-ethyl]-12,12-dimethyl-1,10,14-trioxa-3-aza-dispiro[5.2.5.2]hexadecan-2-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphosgene | HCID 94429 | — |
| Reactant | 9-{2-[(S)-1-(4-Methoxy-phenyl)-ethylamino]-ethyl}-3,3-dimethyl-1,5-dioxa-spiro[5.5]undecan-9-ol | HCID 67995980 | — |
| Product | 3-[(S)-1-(4-methoxy-phenyl)-ethyl]-12,12-dimethyl-1,10,14-trioxa-3-aza-dispiro[5.2.5.2]hexadecan-2-one | HCID 67995695 | 27% |
| Product | 3-[(S)-1-(4-Methoxy-phenyl)-ethyl]-1-oxa-3-aza-spiro[5.5]undecane-2,9-dione | HCID 67996448 | — |
Reaction Steps
The title compound is prepared from 9-{2-[(S)-1-(4-methoxy-phenyl)-ethylamino]-ethyl}-3,3-dimethyl-1,5-dioxa-spiro[5.5]undecan-9-ol and triphosgene following a procedure analogous to that described in Step 4 of Intermediate 2; besides the title compound the intermediate 3-[(S)-1-(4-methoxy-phenyl)-ethyl]-12,12-dimethyl-1,10,14-trioxa-3-aza-dispiro[5.2.5.2]hexadecan-2-one (27% of theory) is also isolated. Yield: 38% of theory; LC (method 4): tR=1.41 min; Mass spectrum (ESI+): m/z=318 [m+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08765744B2 |
| Source dataset | uspto-grants-2014_07 |
| ORD ID | ord-2e9cdd5b851045cf8f9460e8e274b899 |
| Source note | uspto-grants-2014_07 |