Triphosgene → 3-[(S)-1-(3,4-Difluoro-phenyl)-ethyl]-1-oxa-3-aza-spiro[5.5]undecane-2,9-dione

HRID 1615176Notes

Reaction equation

HRID 1615176 reaction equation
FC1C=C([C@@H](NCCC2(O)CCC3(OCC(C)(C)CO3)CC2)C)C=CC=1F.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.[F:40][C:41]1[CH:42]=[C:43]([C@@H:48]([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])[CH3:49])[CH:44]=[CH:45][C:46]=1[F:47]>>[F:40][C:41]1[CH:42]=[C:43]([C@@H:48]([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])[CH3:49])[CH:44]=[CH:45][C:46]=1[F:47]

Participants

4

Reactant 3

HCID 94429TriphosgeneHCID 679958603-[(S)-1-(3,4-difluoro-phenyl)-ethyl]-12,12-dimethyl-1,10,14-trioxa-3-aza-dispiro[5.2.5.2]hexadecan-2-oneHCID 679963469-{2-[(S)-1-(3,4-Difluoro-phenyl)-ethylamino]-ethyl}-3,3-dimethyl-1,5-dioxa-spiro[5.5]undecan-9-ol

Product 1

HCID 565957583-[(S)-1-(3,4-Difluoro-phenyl)-ethyl]-1-oxa-3-aza-spiro[5.5]undecane-2,9-dione

Procedure

The title compound is prepared from 9-{2-[(S)-1-(3,4-difluoro-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; the crude product, a mixture of the title compound and 3-[(S)-1-(3,4-difluoro-phenyl)-ethyl]-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, too. Yield: 68% of theory; LC (method 6): tR=1.14 min; Mass spectrum (ESI+): m/z=324 [M+H]+.

Workup

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  2. additionthat is treated

Sources & evidence

ORD record
ord-1a618c5d1cf145bbb72c6b7be664f819
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

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