N,N-Diethylethanamine trihydrofluoride → Ammonia

HRID 1433302Notes

Reaction equation

HRID 1433302 reaction equation
[Si]([O:8][C@H:9]([C:46]1[CH:47]=[C:48]([OH:53])[CH:49]=[C:50]([OH:52])[CH:51]=1)[CH2:10][NH:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[C:25]([C@@H:30]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[CH2:31][CH2:32][N:33]([CH:37]([CH3:39])[CH3:38])[CH:34]([CH3:36])[CH3:35])[CH:24]=2)=[CH:16][CH:15]=1)(C(C)(C)C)(C)C.CCN(CC)CC.F.F.F>CO.O1CCCC1>[NH3:11].[CH:37]([N:33]([CH:34]([CH3:36])[CH3:35])[CH2:32][CH2:31][C@@H:30]([C:25]1[CH:24]=[C:23]([CH2:22][CH2:21][O:20][C:17]2[CH:16]=[CH:15][C:14]([CH2:13][CH2:12][NH:11][CH2:10][C@@H:9]([C:46]3[CH:47]=[C:48]([OH:53])[CH:49]=[C:50]([OH:52])[CH:51]=3)[OH:8])=[CH:19][CH:18]=2)[CH:28]=[CH:27][C:26]=1[OH:29])[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)([CH3:38])[CH3:39]

Participants

6

Reactant 2

HCID 175505N,N-Diethylethanamine trihydrofluorideHCID 579331935-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({2-[4-(2-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}ethoxy)phenyl]ethyl}amino)ethyl]benzene-1,3-diol

Product 2

HCID 222AmmoniaHCID 579331595-[(1R)-2-({2-[4-(2-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}ethoxy) phenyl]ethyl}amino)-1-hydroxyethyl]benzene-1,3-diol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({2-[4-(2-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}ethoxy)phenyl]ethyl}amino)ethyl]benzene-1,3-diol (Preparation 44, 174 mg, 0.23 mmol) was dissolved in methanol (5 ml) and tetrahydrofuran (10 ml), and triethylaminetrihydrofluoride (0.23 ml, 1.4 mmol) added. The mixture was stirred overnight and then the solvent removed in vacuo. The residue was dissolved in methanol (10 ml) and 880 ammonia (1 ml) and the solvent removed under reduced pressure. This was repeated and the residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (95/5/0.5 to 80/20/2.0 by volume) to furnish the title compound as a foam, 83 mg.

Workup

  1. customthe solvent removed in vacuo
  2. dissolutionThe residue was dissolved in methanol (10 ml)
  3. custom880 ammonia (1 ml) and the solvent removed under reduced pressure
  4. customthe residue was purified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-020b248ce48642f591606493c61b8e7d
Source dataset
uspto-grants-2009_11
Patent number
US07612084B2

Reaction notes

Loading…