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

HRID 1615178Notes

Reaction equation

HRID 1615178 reaction equation
FC(F)OC1C=CC([C@@H](NCCC2(O)CCC3(OCC(C)(C)CO3)CC2)C)=CC=1.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.[F:42][CH:43]([F:72])[O:44][C:45]1[CH:50]=[CH:49][C:48]([C@@H:51]([N:53]2[CH2:58][CH2:57][C:56]3([CH2:70][CH2:69][C:61]4(OCC(C)(C)C[O:62]4)[CH2:60][CH2:59]3)[O:55][C:54]2=[O:71])[CH3:52])=[CH:47][CH:46]=1>>[F:72][CH:43]([F:42])[O:44][C:45]1[CH:50]=[CH:49][C:48]([C@@H:51]([N:53]2[CH2:58][CH2:57][C:56]3([CH2:70][CH2:69][C:61](=[O:62])[CH2:60][CH2:59]3)[O:55][C:54]2=[O:71])[CH3:52])=[CH:47][CH:46]=1

Participants

4

Reactant 3

HCID 94429TriphosgeneHCID 679958319-{2-[(S)-1-(4-Difluoromethoxy-phenyl)-ethylamino]-ethyl}-3,3-dimethyl-1,5-dioxa-spiro[5.5]undecan-9-olHCID 679961453-[(S)-1-(4-difluoromethoxy-phenyl)-ethyl]-12,12-dimethyl-1,10,14-trioxa-3-aza-dispiro[5.2.5.2]hexadecan-2-one

Product 1

HCID 679964913-[(S)-1-(4-Difluoromethoxy-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-difluoromethoxy-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-(4-difluoromethoxy-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: 45% of theory; LC (method 6): tR=1.14 min; Mass spectrum (ESI+): m/z=354 [M+H]+.

Workup

  1. customobtained after
  2. additionthat is treated

Sources & evidence

ORD record
ord-a81b6b3c7ae34ecca18c30a588a53a5c
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

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