Triphosgene → HCID 67996156, compound

HRID 1615181Notes

Reaction equation

ClC1C=CC([C@@H](NCCC2(O)CCC3(OCC(C)(C)CO3)CC2)CC)=CC=1.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.[Cl:40][C:41]1[CH:46]=[CH:45][C:44]([C@@H:47]([N:50]2[CH2:55][CH2:54][C:53]3([CH2:67][CH2:66][C:58]4(OCC(C)(C)C[O:59]4)[CH2:57][CH2:56]3)[O:52][C:51]2=[O:68])[CH2:48][CH3:49])=[CH:43][CH:42]=1>>[Cl:40][C:41]1[CH:46]=[CH:45][C:44]([C@@H:47]([N:50]2[CH2:55][CH2:54][C:53]3([CH2:67][CH2:66][C:58](=[O:59])[CH2:57][CH2:56]3)[O:52][C:51]2=[O:68])[CH2:48][CH3:49])=[CH:43][CH:42]=1

Participants

Reactant 3

HCID 94429Triphosgene

HCID 67996118HCID 67996118, compound

HCID 67996586HCID 67996586, compound

Product 1

HCID 67996156HCID 67996156, compound

Procedure

The title compound is prepared from 9-{2-[(S)-1-(4-chloro-phenyl)-propylamino]-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; the crude product, a mixture of the title compound and 3-[(S)-1-(4-chloro-phenyl)-propyl]-12,12-dimethyl-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: 68% of theory; LC (method 6): tR=1.32 min; Mass spectrum (ESI+): m/z=336/338 (Cl) [M+H]+.

Workup

customobtained after
additionthat is treated

Sources & evidence

ORD record: ord-a7d97cfe6ed74587971d2b3578142e36
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765744B2

Reaction notes

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