Triphosgene → HCID 56595805, compound

HRID 1615189Notes

Reaction equation

HRID 1615189 reaction equation
BrC1C=CC(C2(NCCC3(O)CCC4(OCC(C)(C)CO4)CC3)CC2)=CC=1.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.[Br:40][C:41]1[CH:46]=[CH:45][C:44]([C:47]2([N:50]3[CH2:55][CH2:54][C:53]4([CH2:67][CH2:66][C:58]5(OCC(C)(C)C[O:59]5)[CH2:57][CH2:56]4)[O:52][C:51]3=[O:68])[CH2:49][CH2:48]2)=[CH:43][CH:42]=1>>[Br:40][C:41]1[CH:46]=[CH:45][C:44]([C:47]2([N:50]3[CH2:55][CH2:54][C:53]4([CH2:67][CH2:66][C:58](=[O:59])[CH2:57][CH2:56]4)[O:52][C:51]3=[O:68])[CH2:49][CH2:48]2)=[CH:43][CH:42]=1

Participants

4

Reactant 3

HCID 94429TriphosgeneHCID 67995750HCID 67995750, compoundHCID 67996011HCID 67996011, compound

Product 1

HCID 56595805HCID 56595805, compound

Procedure

The title compound is prepared from 9-{2-[1-(4-bromo-phenyl)-cyclopropylamino]-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)-cyclopropyl]-12,12-dimethyl-1,10,14-trioxa-3-aza-dispiro[5.2.5.2]hexadecan-2-one, obtained thereafter is treated as described in Step 10 of Intermediate 2 to convert the intermediate to the title compound as well. Yield: 19% of theory; LC (method 7): tR=1.37 min; Mass spectrum (ESI+): m/z=378/380 (Br) [M+H]+.

Workup

  1. customobtained
  2. additionthereafter is treated

Sources & evidence

ORD record
ord-844fa8fd82b343e7a85d223428969b0e
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

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