Triphosgene → 3-[(S)-1-(4-methoxy-phenyl)-ethyl]-12,12-dimethyl-1,10,14-trioxa-3-aza-dispiro[5.2.5.2]hexadecan-2-one

HRID 1615172Notes

Reaction equation

HRID 1615172 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([NH:11][CH2:12][CH2:13][C:14]2([OH:27])[CH2:26][CH2:25][C:17]3([O:22][CH2:21][C:20]([CH3:24])([CH3:23])[CH2:19][O:18]3)[CH2:16][CH2:15]2)[CH3:10])=[CH:5][CH:4]=1.Cl[C:29](Cl)([O:31]C(=O)OC(Cl)(Cl)Cl)Cl>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@@H:9]([N:11]2[CH2:12][CH2:13][C:14]3([CH2:15][CH2:16][C:17](=[O:22])[CH2:25][CH2:26]3)[O:27][C:29]2=[O:31])[CH3:10])=[CH:7][CH:8]=1.[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([N:11]2[CH2:12][CH2:13][C:14]3([CH2:15][CH2:16][C:17]4([O:18][CH2:19][C:20]([CH3:23])([CH3:24])[CH2:21][O:22]4)[CH2:25][CH2:26]3)[O:27][C:29]2=[O:31])[CH3:10])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 679959809-{2-[(S)-1-(4-Methoxy-phenyl)-ethylamino]-ethyl}-3,3-dimethyl-1,5-dioxa-spiro[5.5]undecan-9-ol

Product 2

HCID 679956953-[(S)-1-(4-methoxy-phenyl)-ethyl]-12,12-dimethyl-1,10,14-trioxa-3-aza-dispiro[5.2.5.2]hexadecan-2-oneYield 27%HCID 679964483-[(S)-1-(4-Methoxy-phenyl)-ethyl]-1-oxa-3-aza-spiro[5.5]undecane-2,9-dione

Procedure

The title compound is prepared from 9-{2-[(S)-1-(4-methoxy-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-methoxy-phenyl)-ethyl]-12,12-dimethyl-1,10,14-trioxa-3-aza-dispiro[5.2.5.2]hexadecan-2-one (27% of theory) is also isolated. Yield: 38% of theory; LC (method 4): tR=1.41 min; Mass spectrum (ESI+): m/z=318 [m+H]+.

Sources & evidence

ORD record
ord-2e9cdd5b851045cf8f9460e8e274b899
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

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