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

HRID 1615192Notes

Reaction equation

HRID 1615192 reaction equation
CC1(C)COC2(CCC(CCN[C@H](C3C=CC=CC=3C)C)(O)CC2)OC1.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.CC1(C)CO[C:43]2([CH2:63][CH2:62][C:46]3([O:51][C:50](=[O:52])[N:49]([C@H:53]([C:55]4[CH:60]=[CH:59][CH:58]=[CH:57][C:56]=4[CH3:61])[CH3:54])[CH2:48][CH2:47]3)[CH2:45][CH2:44]2)[O:42]C1>>[C:56]1([CH3:61])[CH:57]=[CH:58][CH:59]=[CH:60][C:55]=1[C@@H:53]([N:49]1[CH2:48][CH2:47][C:46]2([CH2:62][CH2:63][C:43](=[O:42])[CH2:44][CH2:45]2)[O:51][C:50]1=[O:52])[CH3:54]

Participants

4

Reactant 3

HCID 94429TriphosgeneHCID 679957183,3-Dimethyl-9-{2-[(S)-1-o-tolyl-ethylamino]-ethyl}-1,5-dioxa-spiro[5.5]undecan-9-olHCID 8666837712,12-di methyl-3-[(S)-1-o-tolyl-ethyl]-1,10,14-trioxa-3-aza-dispiro[5.2.5.2]hexadecan-2-one

Product 1

HCID 704975853-[(S)-1-o-Tolyl-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-o-tolyl-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-di methyl-3-[(S)-1-o-tolyl-ethyl]-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: 17% of theory; LC (method 8): tR=1.23 min; Mass spectrum (ESI+): m/z=302 [M+H]+.

Workup

  1. customobtained
  2. additionthereafter is treated

Sources & evidence

ORD record
ord-730722d1207f45e28df783cfe9b41001
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

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