Triphosgene → 3-[(S)-1-(4-chloro-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-Chloro-phenyl)-ethylamino]-ethyl}-3,3-dimethyl-1,5-dioxa-spiro[5.5]undecan-9-ol	HCID 67996185	—
Product	3-[(S)-1-(4-Chloro-phenyl)-ethyl]-1-oxa-3-aza-spiro[5.5]undecane-2,9-dione	HCID 67996654	—
Product	3-[(S)-1-(4-chloro-phenyl)-ethyl]-12,12-dimethyl-1,10,14-trioxa-3-aza-dispiro[5.2.5.2]hexadecan-2-one	HCID 70498015	35%

Reaction Steps

The title compound is prepared from 9-{2-[(S)-1-(4-chloro-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-chloro-phenyl)-ethyl]-12,12-dimethyl-1,10,14-trioxa-3-aza-dispiro[5.2.5.2]hexadecan-2-one (35% of theory) is also isolated. Yield: 23% of theory; LC (method 4): tR=1.51 min; Mass spectrum (ESI+): m/z=322/324 (Cl) [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08765744B2
Source dataset	uspto-grants-2014_07
ORD ID	ord-55b51bb38bb4472680e85477f5294c7b
Source note	uspto-grants-2014_07