Potassium Iodide → Ammonia

HRID 1433274Notes

Reaction equation

HRID 1433274 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([CH:40]=[CH:41][CH:42]=1)[O:7][CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[C:14]([C@@H:16]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:17][CH2:18][N:19]([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])[CH:15]=1.[I-].[K+].C(=O)([O-])O.[Na+].[CH2:50]([O:57][C:58]1[CH:63]=[CH:62][C:61]([C@@H:64]([O:67][Si:68]([C:71]([CH3:74])([CH3:73])[CH3:72])([CH3:70])[CH3:69])[CH2:65]Br)=[CH:60][C:59]=1[CH2:75][OH:76])[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>C(#N)CC.C(OCC)(=O)C.O>[NH3:1].[CH2:50]([O:57][C:58]1[CH:63]=[CH:62][C:61]([C@@H:64]([O:67][Si:68]([C:71]([CH3:73])([CH3:72])[CH3:74])([CH3:69])[CH3:70])[CH2:65][NH:1][CH2:2][CH2:3][C:4]2[CH:42]=[CH:41][CH:40]=[C:6]([O:7][CH2:8][CH2:9][C:10]3[CH:11]=[CH:12][C:13]([O:32][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[C:14]([C@@H:16]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH2:17][CH2:18][N:19]([CH:20]([CH3:22])[CH3:21])[CH:23]([CH3:25])[CH3:24])[CH:15]=3)[CH:5]=2)=[CH:60][C:59]=1[CH2:75][OH:76])[C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1

Participants

9

Reactant 4

HCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 12988834[2-(benzyloxy)-5-((1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)phenyl]methanolHCID 57933181(3R)-3-[5-{2-[3-(2-aminoethyl)phenoxy]ethyl}-2-(benzyloxy)phenyl]-N,N-diisopropyl-3-phenylpropan-1-amine

Product 2

HCID 222AmmoniaHCID 57933183{2-(benzyloxy)-5-[(1R)-2-({2-[3-(2-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}ethoxy)phenyl]ethyl}amino)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanol

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 7854PropionitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

(3R)-3-[5-{2-[3-(2-aminoethyl)phenoxy]ethyl}-2-(benzyloxy)phenyl]-N,N-diisopropyl-3-phenylpropan-1-amine (Preparation 38, 470 mg, 0.72 mmol), potassium iodide (120 mg, 0.72 mmol), sodium hydrogen carbonate (240 mg, 2.9 mmol) and {2-(benzyloxy)-5-[(1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]phenyl}methanol (Prepared according to WO2004/032921, 325 mg, 0.72 mmol) were stirred in propionitrile at 100° C. for 24 hours under nitrogen. After cooling to room temperature, water (100 ml) and ethyl acetate (100 ml) were added, organics separated and washed with brine (100 ml), dried (magnesium sulphate) and solvent removed in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (100/0/0 to 8511511.5 by volume) to furnish the title compound as a brown glass, 450 mg.

Workup

  1. customorganics separated
  2. washwashed with brine (100 ml)
  3. dry with materialdried (magnesium sulphate) and solvent
  4. customremoved in vacuo
  5. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-6ac37655c58748ea9bad700efd1fa687
Source dataset
uspto-grants-2009_11
Patent number
US07612084B2

Reaction notes

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