Ammonium formate → Ammonia

HRID 1433289Notes

Reaction equation

HRID 1433289 reaction equation
[C:1]([O:5][C:6](=[O:52])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19]/[CH:20]=[CH:21]/[C:22]2[CH:27]=[CH:26][C:25]([O:28]CC3C=CC=CC=3)=[C:24]([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:23]=2)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>C(O)C.[OH-].[Pd+2].[OH-]>[NH3:7].[C:1]([O:5][C:6](=[O:52])[NH:7][CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([C@@H:36]([C:46]3[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=3)[CH2:37][CH2:38][N:39]([CH:43]([CH3:44])[CH3:45])[CH:40]([CH3:42])[CH3:41])[CH:23]=2)=[CH:14][CH:15]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 57933225tert-butyl[2-(4-{[(4E)-5-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}pent-4-en-1-yl]oxy}phenyl)ethyl]carbamate

Product 2

HCID 222AmmoniaHCID 57933162tert-butyl(2-{4-[(5-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}pentyl)oxy]phenyl}ethyl)carbamate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

Tert-butyl[2-(4-{[(4E)-5-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}pent-4-en-1-yl]oxy}phenyl)ethyl]carbamate (Preparation 57, 2.5 g, 3.5 mmol) was dissolved in ethanol (50 ml) and palladium hydroxide (20% by weight on carbon, 600 mg, 0.84 mmol) and ammonium formate (2.0 g, 30 mmol) were added and stirred at 90° C. for 1 hour. Reaction was cooled and filtered through arbocel and the solvent removed in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (95/5/0.5 to 90/10/1 by volume) to furnish the title compound as a white foam, 1.66 g

Workup

  1. customReaction
  2. temperaturewas cooled
  3. filtrationfiltered through arbocel
  4. customthe solvent removed in vacuo
  5. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-9b7478f13ed240a7b1753c46cc285576
Source dataset
uspto-grants-2009_11
Patent number
US07612084B2

Reaction notes

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