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

HRID 1615173Notes

Reaction equation

HRID 1615173 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][CH2:11][CH2:12][C:13]2([OH:26])[CH2:25][CH2:24][C:16]3([O:21][CH2:20][C:19]([CH3:23])([CH3:22])[CH2:18][O:17]3)[CH2:15][CH2:14]2)[CH3:9])=[CH:4][CH:3]=1.Cl[C:28](Cl)([O:30]C(=O)OC(Cl)(Cl)Cl)Cl>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([N:10]2[CH2:11][CH2:12][C:13]3([CH2:14][CH2:15][C:16](=[O:21])[CH2:24][CH2:25]3)[O:26][C:28]2=[O:30])[CH3:9])=[CH:6][CH:7]=1.[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:11][CH2:12][C:13]3([CH2:14][CH2:15][C:16]4([O:17][CH2:18][C:19]([CH3:23])([CH3:22])[CH2:20][O:21]4)[CH2:24][CH2:25]3)[O:26][C:28]2=[O:30])[CH3:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 679961859-{2-[(S)-1-(4-Chloro-phenyl)-ethylamino]-ethyl}-3,3-dimethyl-1,5-dioxa-spiro[5.5]undecan-9-ol

Product 2

HCID 679966543-[(S)-1-(4-Chloro-phenyl)-ethyl]-1-oxa-3-aza-spiro[5.5]undecane-2,9-dioneHCID 704980153-[(S)-1-(4-chloro-phenyl)-ethyl]-12,12-dimethyl-1,10,14-trioxa-3-aza-dispiro[5.2.5.2]hexadecan-2-oneYield 35%

Procedure

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]+.

Sources & evidence

ORD record
ord-55b51bb38bb4472680e85477f5294c7b
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

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