Ammonium formate → 4-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({2-[4-(4-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}butoxy)phenyl]ethyl}amino)ethyl]-2-(hydroxymethyl)phenol

HRID 1433293Notes

Reaction equation

HRID 1433293 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:54][Si:55]([C:58]([CH3:61])([CH3:60])[CH3:59])([CH3:57])[CH3:56])[CH2:16][NH:17][CH2:18][CH2:19][C:20]2[CH:53]=[CH:52][C:23]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]3[CH:34]=[CH:33][C:32]([OH:35])=[C:31]([C@@H:36]([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[CH2:37][CH2:38][N:39]([CH:43]([CH3:45])[CH3:44])[CH:40]([CH3:42])[CH3:41])[CH:30]=3)=[CH:22][CH:21]=2)=[CH:11][C:10]=1[CH2:62][OH:63])C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[OH-].[OH-].[Pd+2]>[Si:55]([O:54][C@H:15]([C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([CH2:62][OH:63])[CH:11]=1)[CH2:16][NH:17][CH2:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([O:24][CH2:25][CH2:26][CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([OH:35])=[C:31]([C@@H:36]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[CH2:37][CH2:38][N:39]([CH:43]([CH3:45])[CH3:44])[CH:40]([CH3:42])[CH3:41])[CH:30]=2)=[CH:52][CH:53]=1)([C:58]([CH3:61])([CH3:59])[CH3:60])([CH3:57])[CH3:56]

Participants

5

Reactant 2

HCID 2723923Ammonium formate2×HCID 579331564-{4-[4-(2-{[(2R)-2-[4-(benzyloxy)-3-(hydroxymethyl)phenyl]-2-{[tert-butyl(dimethyl)silyl]oxy}ethyl]amino}ethyl)phenoxy]butyl}-2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenol

Product 1

HCID 579332274-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-2-({2-[4-(4-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}butoxy)phenyl]ethyl}amino)ethyl]-2-(hydroxymethyl)phenol

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst2×HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

4-{4-[4-(2-{[(2R)-2-[4-(benzyloxy)-3-(hydroxymethyl)phenyl]-2-{[tert-butyl(dimethyl)silyl]oxy}ethyl]amino}ethyl)phenoxy]butyl}-2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenol (Preparation 62, 388 mg, 0.44 mmol) was dissolved in ethanol (5 ml) and ammonium formate (280 mg, 4.44 mmol) and 20% palladium hydroxide on carbon (58 mg) added. The stirred reaction was heated at 85° C. for 18 hours. After cooling to room temperature, further ammonium formate (140 mg, 2.22 mmol) and 20% palladium hydroxide on carbon (20 mg) were added and mixture stirred at 85° C. for 3 hours. Reaction mixture was then cooled and filtered through Arbocel™, the filtrate was collected and the solvent removed in vacuo to furnish the title compound as a glass, 311 mg.

Workup

  1. customThe stirred reaction
  2. temperatureAfter cooling to room temperature
  3. customReaction mixture
  4. temperaturewas then cooled
  5. filtrationfiltered through Arbocel™
  6. customthe filtrate was collected
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-a9ad0e6d77904bf7aa72233a07378bc6
Source dataset
uspto-grants-2009_11
Patent number
US07612084B2

Reaction notes

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