HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphosgene → 3-[(S)-(4-bromo-phenyl)-cyclopropyl-methyl]-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)-(4-Bromo-phenyl)-cyclopropyl-methyl]-amino}-ethyl)-3,3-dimethyl-1,5-dioxa-spiro[5.5]undecan-9-ol | HCID 67995925 | — |
| Product | 3-[(S)-(4-bromo-phenyl)-cyclopropyl-methyl]-12,12-dimethyl-1,10,14-trioxa-3-aza-dispiro[5.2.5.2]hexadecan-2-one | HCID 67995758 | 37% |
| Product | 3-[(S)-(4-Bromo-phenyl)-cyclopropyl-methyl]-1-oxa-3-aza-spiro[5.5]undecane-2,9-dione | HCID 67996364 | — |
Reaction Steps
The title compound is prepared from 9-(2-{[(S)-(4-bromo-phenyl)-cyclopropyl-methyl]-amino}-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)-(4-bromo-phenyl)-cyclopropyl-methyl]-12,12-dimethyl-1,10,14-trioxa-3-aza-dispiro[5.2.5.2]hexadecan-2-one (37% of theory) is also isolated. Yield: 25% of theory; LC (method 4): tR=1.59 min; Mass spectrum (ESI+): m/z=392/394 (Br) [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08765744B2 |
| Source dataset | uspto-grants-2014_07 |
| ORD ID | ord-e9ccbf43c0b1466dace14a00f6fb86ac |
| Source note | uspto-grants-2014_07 |