Triphosgene → 3-[(S)-1-(2,5-Dimethyl-phenyl)-ethyl]-1-oxa-3-aza-spiro[5.5]undecane-2,9-dione

HRID 1615179Notes

Reaction equation

HRID 1615179 reaction equation
CC1C=CC(C)=CC=1[C@@H](NCCC1(O)CCC2(OCC(C)(C)CO2)CC1)C.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.[CH3:40][C:41]1[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][C:42]=1[C@@H:48]([N:50]1[CH2:55][CH2:54][C:53]2([CH2:67][CH2:66][C:58]3(OCC(C)(C)C[O:59]3)[CH2:57][CH2:56]2)[O:52][C:51]1=[O:68])[CH3:49]>>[CH3:40][C:41]1[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][C:42]=1[C@@H:48]([N:50]1[CH2:55][CH2:54][C:53]2([CH2:56][CH2:57][C:58](=[O:59])[CH2:66][CH2:67]2)[O:52][C:51]1=[O:68])[CH3:49]

Participants

4

Reactant 3

HCID 94429TriphosgeneHCID 679958179-{2-[(S)-1-(2,5-Dimethyl-phenyl)-ethylamino]-ethyl}-3,3-dimethyl-1,5-dioxa-spiro[5.5]undecan-9-olHCID 679966913-[(S)-1-(2,5-dimethyl-phenyl)-ethyl]-12,12-dimethyl-1,10,14-trioxa-3-aza-dispiro[5.2.5.2]hexadecan-2-one

Product 1

HCID 679960763-[(S)-1-(2,5-Dimethyl-phenyl)-ethyl]-1-oxa-3-aza-spiro[5.5]undecane-2,9-dione

Procedure

The title compound is prepared from 9-{2-[(S)-1-(2,5-dimethyl-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-(2,5-dimethyl-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: 49% of theory; Mass spectrum (ESI+): m/z=316 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ 1.47 (d, J=7.2 Hz, 3H), 1.79-2.00 (m, 5H), 2.05-2.13 (m, 1H), 2.15-2.25 (m, 2H) superimposed by 2.20 (s, 3H) and 2.22 (s, 3H), 2.44-2.55 (m, 2H), 2.70-2.78 (m, 1H), 3.16-3.24 (m, 1H), 5.48 (q, J=7.2 Hz, 1H), 7.02 (dm, J=7.8 Hz, 1H), 7.08 (broad s, 1H), 7.12 (d, J=7.8 Hz, 1H).

Workup

  1. customobtained after
  2. additionthat is treated

Sources & evidence

ORD record
ord-2a2da1b540484790bda78bc3f31407a6
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

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