Tributyltin azide → HCID 86641747, compound

HRID 1798477Notes

Reaction equation

HRID 1798477 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH:49]=[C:50]([CH2:52][CH2:53][CH2:54][O:55][CH3:56])[CH:51]=1)[CH2:10][N:11]([CH:46]1[CH2:48][CH2:47]1)[C:12]([C@@H:14]1[C@@H:19]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][O:29][C:30]3[C:35]([Cl:36])=[CH:34][C:33]([CH3:37])=[CH:32][C:31]=3[Cl:38])=[CH:22][CH:21]=2)[CH2:18][CH2:17][N:16]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:15]1)=[O:13])#[N:2].C([Sn]([N:70]=[N+:71]=[N-:72])(CCCC)CCCC)CCC>O1CCOCC1.CCOC(C)=O>[CH:46]1([N:11]([CH2:10][C:9]2[CH:8]=[C:7]([O:6][CH2:5][CH2:4][CH2:3][C:1]3[N:70]=[N:71][NH:72][N:2]=3)[CH:51]=[C:50]([CH2:52][CH2:53][CH2:54][O:55][CH3:56])[CH:49]=2)[C:12]([C@@H:14]2[C@@H:19]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH2:28][O:29][C:30]4[C:35]([Cl:36])=[CH:34][C:33]([CH3:37])=[CH:32][C:31]=4[Cl:38])=[CH:22][CH:21]=3)[CH2:18][CH2:17][N:16]([C:39]([O:41][C:42]([CH3:43])([CH3:44])[CH3:45])=[O:40])[CH2:15]2)=[O:13])[CH2:48][CH2:47]1

Participants

5

Reactant 2

HCID 4984872Tributyltin azideHCID 86641746HCID 86641746, compound

Product 1

HCID 86641747HCID 86641747, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of tert-butyl (3R,4S)-3-{[[3-(3-cyanopropoxy)-5-(3-methoxy-propyl)benzyl](cyclopropyl)amino]carbonyl}-4-{4-[2-(2,6-dichloro-4-methylphen-oxy)ethoxy]-phenyl}piperidine-1-carboxylate (1 eq.) from the previous step in dioxane (0.17 M) was added tri-n-butyltin azide (3 eq.). The reaction was heated to 150° C. in a sealed tube for 18 h. After cooling down to rt, the reaction was diluted with EtOAc. The organic extract was washed with saturated aqueous NH4Cl solution, brine, dried over MgSO4, and concentrated in vacuo. The crude product was purified by flash column chromatography (SiO2, first 50% EtOAc in Hex to 100% EtOAc, then 5% MeOH in DCM) to afford the title compound as an oil.

Workup

  1. temperatureAfter cooling down to rt
  2. extractionThe organic extract
  3. washwas washed with saturated aqueous NH4Cl solution, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash column chromatography (SiO2, first 50% EtOAc in Hex to 100% EtOAc

Sources & evidence

ORD record
ord-784389d5604d430592dd0c381638bcf6
Source dataset
uspto-grants-2013_01
Patent number
US08343968B2

Reaction notes

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