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

HRID 1615187Notes

Reaction equation

HRID 1615187 reaction equation
COC1C=C([C@@H](NCCC2(O)CCC3(OCC(C)(C)CO3)CC2)C)C=CC=1.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.[CH3:40][O:41][C:42]1[CH:43]=[C:44]([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:45]=[CH:46][CH:47]=1>>[CH3:40][O:41][C:42]1[CH:43]=[C:44]([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:45]=[CH:46][CH:47]=1

Participants

4

Reactant 3

HCID 94429TriphosgeneHCID 679958989-{2-[(S)-1-(3-Methoxy-phenyl)-ethylamino]-ethyl}-3,3-dimethyl-1,5-dioxa-spiro[5.5]undecan-9-olHCID 679961043-[(S)-1-(3-methoxy-phenyl)-ethyl]-12,12-dimethyl-1,10,14-trioxa-3-aza-dispiro[5.2.5.2]hexadecan-2-one

Product 1

HCID 679959543-[(S)-1-(3-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-(3-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; the crude product, a mixture of the title compound and 3-[(S)-1-(3-methoxy-phenyl)-ethyl]-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: 41% of theory; LC (method 6): tR=1.11 min; Mass spectrum (ESI+): m/z=318 [M+H]+.

Workup

  1. customobtained
  2. additionthereafter is treated

Sources & evidence

ORD record
ord-8c087b52dc74445281d416476ceef57d
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

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