Triphosgene → HCID 67995933, compound

HRID 1615185Notes

Reaction equation

HRID 1615185 reaction equation
CC1(C)COC2(CCC(CCN[C@H](C3C=CC4C(=CC=CC=4)C=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:67]=[CH:66][C:65]5[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=5)[CH:59]=4)[CH3:57])[CH2:51][CH2:50]3)[CH2:48][CH2:47]2)[O:45]C1>>[CH:59]1[C:60]2[C:65](=[CH:64][CH:63]=[CH:62][CH:61]=2)[CH:66]=[CH:67][C:58]=1[C@@H:56]([N:52]1[CH2:51][CH2:50][C:49]2([CH2:68][CH2:69][C:46](=[O:45])[CH2:47][CH2:48]2)[O:54][C:53]1=[O:55])[CH3:57]

Participants

4

Reactant 3

HCID 94429TriphosgeneHCID 67996101HCID 67996101, compoundHCID 70498295HCID 70498295, compound

Product 1

HCID 67995933HCID 67995933, compound

Procedure

The title compound is prepared from 3,3-dimethyl-9-{2-[(S)-1-naphthalen-2-yl-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-naphthalen-2-yl-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: 56% of theory; LC (method 6): tR=1.34 min; Mass spectrum (ESI+): m/z=338 [M+H]+.

Workup

  1. customobtained
  2. additionthereafter is treated

Sources & evidence

ORD record
ord-db370ec0001f4c5a9628ae7a104442a2
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

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