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

HRID 1615145Notes

Reaction equation

HRID 1615145 reaction equation
BrC1C=CC(C(NCCC2(O)CCC3(OCC(C)(C)CO3)CC2)(C)C)=CC=1.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.[Br:40][C:41]1[CH:46]=[CH:45][C:44]([C: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])([CH3:49])[CH3:48])=[CH:43][CH:42]=1>>[Br:40][C:41]1[CH:46]=[CH:45][C:44]([C: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])([CH3:49])[CH3:48])=[CH:43][CH:42]=1

Participants

4

Reactant 3

HCID 94429TriphosgeneHCID 679956463-[1-(4-Bromo-phenyl)-1-methyl-ethyl]-12,12-dimethyl-1,10,14-trioxa-3-aza-dispiro[5.2.5.2]hexadecan-2-oneHCID 679959639-{2-[1-(4-Bromo-phenyl)-1-methyl-ethylamino]-ethyl}-3,3-dimethyl-1,5-dioxa-spiro[5.5]undecan-9-ol

Product 1

HCID 679957543-[1-(4-Bromo-phenyl)-1-methyl-ethyl]-1-oxa-3-aza-spiro[5.5]undecane-2,9-dione

Procedure

The title compound is prepared from 9-{2-[1-(4-bromo-phenyl)-1-methyl-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-[1-(4-bromo-phenyl)-1-methyl-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 as well. Yield: 37% of theory; LC (method 6): tR=1.28 min; Mass spectrum (ESI+): m/z=380/382 (Br) [m+H]+.

Workup

  1. customobtained after
  2. additionthat is treated

Sources & evidence

ORD record
ord-04bc83e2bcdc4b07b54a282f44d428a9
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

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