Triphosgene → HCID 56595801, compound

HRID 1615177Notes

Reaction equation

HRID 1615177 reaction equation
CC1(C)COC2(CCC(CCN[C@H](C3C=CC(C(F)(F)F)=CC=3)C)(O)CC2)OC1.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.CC1(C)CO[C:46]2([CH2:69][CH2:68][C:49]3([O:54][C:53](=[O:55])[N:52]([C@H:56]([C:58]4[CH:63]=[CH:62][C:61]([C:64]([F:67])([F:66])[F:65])=[CH:60][CH:59]=4)[CH3:57])[CH2:51][CH2:50]3)[CH2:48][CH2:47]2)[O:45]C1>>[F:67][C:64]([F:65])([F:66])[C:61]1[CH:62]=[CH:63][C:58]([C@@H:56]([N:52]2[CH2:51][CH2:50][C:49]3([CH2:68][CH2:69][C:46](=[O:45])[CH2:47][CH2:48]3)[O:54][C:53]2=[O:55])[CH3:57])=[CH:59][CH:60]=1

Participants

4

Reactant 3

HCID 94429TriphosgeneHCID 67995832HCID 67995832, compoundHCID 67995834HCID 67995834, compound

Product 1

HCID 56595801HCID 56595801, compound

Procedure

The title compound is prepared from 3,3-dimethyl-9-{2-[(S)-1-(4-trifluoromethyl-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-trifluoromethyl-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, too. Yield: 67% of theory; LC (method 6): tR=1.28 min; Mass spectrum (ESI+): m/z=356 [M+H]+.

Workup

  1. customobtained after
  2. additionthat is treated

Sources & evidence

ORD record
ord-96b9bdb0e5e84806af0ee1e140488fca
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

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