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

HRID 1615180Notes

Reaction equation

HRID 1615180 reaction equation
CC1(C)COC2(CCC(CCN[C@H](C3C=CC(OC(F)(F)F)=CC=3)C)(O)CC2)OC1.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.CC1(C)CO[C:47]2([CH2:71][CH2:70][C:50]3([O:55][C:54](=[O:56])[N:53]([C@H:57]([C:59]4[CH:64]=[CH:63][C:62]([O:65][C:66]([F:69])([F:68])[F:67])=[CH:61][CH:60]=4)[CH3:58])[CH2:52][CH2:51]3)[CH2:49][CH2:48]2)[O:46]C1>>[F:69][C:66]([F:67])([F:68])[O:65][C:62]1[CH:63]=[CH:64][C:59]([C@@H:57]([N:53]2[CH2:52][CH2:51][C:50]3([CH2:49][CH2:48][C:47](=[O:46])[CH2:71][CH2:70]3)[O:55][C:54]2=[O:56])[CH3:58])=[CH:60][CH:61]=1

Participants

4

Reactant 3

HCID 94429TriphosgeneHCID 679962903,3-Dimethyl-9-{2-[(S)-1-(4-trifluoromethoxy-phenyl)-ethylamino]-ethyl}-1,5-dioxa-spiro[5.5]undecan-9-olHCID 7049833012,12-dimethyl-3-[(S)-1-(4-trifluoromethoxy-phenyl)-ethyl]-1,10,14-trioxa-3-aza-dispiro[5.2.5.2]hexadecan-2-one

Product 1

HCID 679964843-[(S)-1-(4-Trifluoromethoxy-phenyl)-ethyl]-1-oxa-3-aza-spiro[5.5]undecane-2,9-dione

Procedure

The title compound is prepared from 3,3-dimethyl-9-{2-[(S)-1-(4-trifluoromethoxy-phenyl)-ethylamino]-ethyl}-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 12,12-dimethyl-3-[(S)-1-(4-trifluoromethoxy-phenyl)-ethyl]-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: 57% of theory; LC (method 6): tR=1.33 min; Mass spectrum (ESI+): m/z=372 [M+H]+.

Workup

  1. customobtained after
  2. additionthat is treated

Sources & evidence

ORD record
ord-fde85fdf83b4476aaae2a91d47a03bfa
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

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