Triphosgene → 3-[(S)-1-(4-Bromo-phenyl)-ethyl]-1-oxa-3-aza-spiro[5.5]undecane-2,9-dione

HRID 1615115Notes

Reaction equation

HRID 1615115 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][CH2:11][CH2:12][C:13]2([OH:23])[CH2:22][CH2:21][C:16]3([O:20]CCO3)[CH2:15][CH2:14]2)[CH3:9])=[CH:4][CH:3]=1.Cl[C:25](Cl)([O:27]C(=O)OC(Cl)(Cl)Cl)Cl>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([N:10]2[CH2:11][CH2:12][C:13]3([CH2:14][CH2:15][C:16](=[O:20])[CH2:21][CH2:22]3)[O:23][C:25]2=[O:27])[CH3:9])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 94429TriphosgeneHCID 679963538-{2-[(S)-1-(4-bromo-phenyl)-ethylamino]-ethyl}-1,4-dioxa-spiro[4.5]decan-8-ol

Product 1

HCID 565957523-[(S)-1-(4-Bromo-phenyl)-ethyl]-1-oxa-3-aza-spiro[5.5]undecane-2,9-dioneYield 6%

Procedure

The title compounds are prepared from 8-{2-[(S)-1-(4-bromo-phenyl)-ethylamino]-ethyl}-1,4-dioxa-spiro[4.5]decan-8-ol and triphosgene following a procedure analogous to that described in step 3 of Intermediate 1. The ketal group is partially cleaved under these conditions to give a mixture of the title compounds that is separated by chromatography on silica gel (cyclohexane/ethyl acetate 9:1→1:1). 11-[(S)-1-(4-bromo-phenyl)-ethyl]-1,4,9-trioxa-11-aza-dispiro[4.2.5.2]pentadecan-10-one: Yield: 6% of theory; LC (method 1): tR=3.65 min; Mass spectrum (ESI+): m/z=410/412 (Br) [M+H]+.

Workup

  1. customto give
  2. customthat is separated by chromatography on silica gel (cyclohexane/ethyl acetate 9:1→1:1)

Sources & evidence

ORD record
ord-ccf6caaee70d4cc7b573107baf7bf229
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

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