Triphosgene → HCID 56595804, compound

HRID 1615188Notes

Reaction equation

HRID 1615188 reaction equation
[C@@H]1(NCCC2(O)CCC3(OCC(C)(C)CO3)CC2)C2C(=CC=CC=2)CC1.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.[C@@H:39]1([N:48]2[CH2:53][CH2:52][C:51]3([CH2:65][CH2:64][C:56]4(OCC(C)(C)C[O:57]4)[CH2:55][CH2:54]3)[O:50][C:49]2=[O:66])[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH2:41][CH2:40]1>>[C@@H:39]1([N:48]2[CH2:53][CH2:52][C:51]3([CH2:54][CH2:55][C:56](=[O:57])[CH2:64][CH2:65]3)[O:50][C:49]2=[O:66])[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH2:41][CH2:40]1

Participants

4

Reactant 3

HCID 94429TriphosgeneHCID 67996191HCID 67996191, compoundHCID 67996264HCID 67996264, compound

Product 1

HCID 56595804HCID 56595804, compound

Procedure

The title compound is prepared from 9-{2-[(S)-indan-1-ylamino]-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)-indan-1-yl]-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: 44% of theory; LC (method 6): tR=1.16 min; Mass spectrum (ESI+): m/z=300 [M+H]+.

Workup

  1. customobtained
  2. additionthereafter is treated

Sources & evidence

ORD record
ord-b9588d8f09b748e79e6c1475840f4329
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

Loading…