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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1615174Generated: November 1, 2026

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

https://huagongshe.com/reaction/1615174

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriphosgeneHCID 94429—
Reactant9-(2-{[(S)-(4-Bromo-phenyl)-cyclopropyl-methyl]-amino}-ethyl)-3,3-dimethyl-1,5-dioxa-spiro[5.5]undecan-9-olHCID 67995925—
Product3-[(S)-(4-bromo-phenyl)-cyclopropyl-methyl]-12,12-dimethyl-1,10,14-trioxa-3-aza-dispiro[5.2.5.2]hexadecan-2-oneHCID 6799575837%
Product3-[(S)-(4-Bromo-phenyl)-cyclopropyl-methyl]-1-oxa-3-aza-spiro[5.5]undecane-2,9-dioneHCID 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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08765744B2
Source datasetuspto-grants-2014_07
ORD IDord-e9ccbf43c0b1466dace14a00f6fb86ac
Source noteuspto-grants-2014_07