Potassium Iodide → Ammonia

HRID 1433277Notes

Reaction equation

HRID 1433277 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][C:6]1[CH:44]=[CH:43][C:9]([O:10][CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[C:17]([C@@H:19]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:20][CH2:21][N:22]([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])[CH:18]=2)=[CH:8][CH:7]=1.[CH2:45]([O:52][C:53]1[CH:54]=[C:55]([C@@H:67]([O:70][Si:71]([C:74]([CH3:77])([CH3:76])[CH3:75])([CH3:73])[CH3:72])[CH2:68]Br)[CH:56]=[C:57]([O:59][CH2:60][C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[CH:58]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.[I-].[K+].C(=O)([O-])O.[Na+].C(#N)CC>C(OCC)(=O)C.O>[NH3:3].[CH2:36]([O:35][C:16]1[CH:15]=[CH:14][C:13]([CH2:12][CH2:11][O:10][C:9]2[CH:43]=[CH:44][C:6]([CH2:5][CH2:4][NH:3][CH2:68][C@@H:67]([C:55]3[CH:54]=[C:53]([O:52][CH2:45][C:46]4[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=4)[CH:58]=[C:57]([O:59][CH2:60][C:61]4[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=4)[CH:56]=3)[O:70][Si:71]([C:74]([CH3:77])([CH3:76])[CH3:75])([CH3:73])[CH3:72])=[CH:7][CH:8]=2)=[CH:18][C:17]=1[C@@H:19]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[CH2:20][CH2:21][N:22]([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

9

Reactant 5

HCID 4875Potassium IodideHCID 7854PropionitrileHCID 516892Sodium BicarbonateHCID 57683377{(1R)-1-[3,5-bis(benzyloxy)phenyl]-2-bromoethoxy}(tert-butyl)dimethylsilaneHCID 86616485(3R)-3-[5-{2-[4-(2-aminoethyl)phenoxy]ethyl}-2-(benzyloxy)phenyl]-N,N-diisopropyl-3-phenylpropan-1-amine bis hydrochloride salt

Product 2

HCID 222AmmoniaHCID 57933155(3R)-3-[2-(benzyloxy)-5-{2-[4-(2-{[(2R)-2-[3,5-bis(benzyloxy)phenyl]-2-{[tert-butyl(dimethyl)silyl]oxy}ethyl]amino}ethyl)phenoxy]ethyl}phenyl]-N,N-diisopropyl-3-phenylpropan-1-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

(3R)-3-[5-{2-[4-(2-aminoethyl)phenoxy]ethyl}-2-(benzyloxy)phenyl]-N,N-diisopropyl-3-phenylpropan-1-amine bis hydrochloride salt (Preparation 42, 600 mg, 0.94 mmol), {(1R)-1-[3,5-bis(benzyloxy)phenyl]-2-bromoethoxy}(tert-butyl)dimethylsilane (Prepared according to US2005/222128, 500 mg, 0.94 mmol), potassium iodide (160 mg, 0.94 mmol), sodium hydrogen carbonate (480 mg, 5.65 mmol) were added to propionitrile (10 ml) and stirred at 100° C. under nitrogen overnight. The mixture was cooled and water (75 ml) and ethyl acetate (75 ml) were added. Organics were separated and washed with brine (25 ml), dried (magnesium sulphate) and the solvent removed in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (99/1/0.1 to 90/10/1 by volume) to furnish the title compound as a gum, 346 mg.

Workup

  1. temperatureThe mixture was cooled
  2. customOrganics were separated
  3. washwashed with brine (25 ml)
  4. dry with materialdried (magnesium sulphate)
  5. customthe solvent removed in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-c2e413cb37d94546bc928e0e57fba51e
Source dataset
uspto-grants-2009_11
Patent number
US07612084B2

Reaction notes

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