Ammonium formate → di-tert-butyl(8-{3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-hydroxyphenyl}octyl)imidodicarbonate

HRID 1433285Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]/[CH:22]=[CH:23]/[C:24]1[CH:29]=[CH:28][C:27]([O:30]CC2C=CC=CC=2)=[C:26]([C@@H:38]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH2:39][CH2:40][N:41]([CH:45]([CH3:47])[CH3:46])[CH:42]([CH3:44])[CH3:43])[CH:25]=1)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>C(O)C.[OH-].[Pd+2].[OH-]>[C:1]([O:5][C:6]([N:8]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[C:26]([C@@H:38]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH2:39][CH2:40][N:41]([CH:45]([CH3:46])[CH3:47])[CH:42]([CH3:44])[CH3:43])[CH:25]=1)[C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

di-tert-butyl[(7E)-8-{4-(benzyloxy)-3-[(1R)-3-(diisopropylamino)-1-phenylpropyl]phenyl}oct-7-en-1-yl]imidodicarbonate (Preparation 51, 530 mg, 0.73 mmol), palladium hydroxide (20% by weight on carbon, 100 mg, 0.14 mmol) and ammonium formate (1.1 g, 17 mmol) were dissolved in ethanol (20 ml) and heated to 70° C. for 3 hours. Reaction mixture was cooled and filtered and the solvent removed in vacuo to yield the title compound as a clear oil, 340 mg.

Workup

customReaction mixture
temperaturewas cooled
filtrationfiltered
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-ce63464b2d254fcba55c2f1f5c4a762b
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612084B2

Reaction notes

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