HCID 53979657, compound → HCID 53747305, compound

HRID 989641Notes

Reaction equation

HRID 989641 reaction equation
C(OC([NH:11][C:12]1[CH:29]=[CH:28][C:15]2[CH2:16][CH:17]([CH2:23][C:24]([O:26][CH3:27])=[O:25])[C:18](=[O:22])[N:19]([CH3:21])[CH2:20][C:14]=2[CH:13]=1)=O)C1C=CC=CC=1>[OH-].[OH-].[Pd+2].CC(O)=O>[NH2:11][C:12]1[CH:29]=[CH:28][C:15]2[CH2:16][CH:17]([CH2:23][C:24]([O:26][CH3:27])=[O:25])[C:18](=[O:22])[N:19]([CH3:21])[CH2:20][C:14]=2[CH:13]=1

Participants

4

Reactant 1

HCID 53979657HCID 53979657, compound

Product 1

HCID 53747305HCID 53747305, compoundYield 100.8%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of methyl (±)-8-[(benzyloxycarbonyl)amino]-2-methyl-3-oxo-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetate (1.5 g), Pearlman's catalyst (0.30 g), and warm AcOH (300 mL) was stirred under H2 (balloon pressure). After 90 min, the mixture was filtered to remove the catalyst, and the filtrate was concentrated to give the title compound as a viscous oil (1 g, 100%): 1H NMR (CDCl3) δ7.00 (br s, 2H), 6.88 (d, J=8.1 Hz, 1H), 6.57 (dd, J=8.1, 2.3 Hz, 1H), 6.43 (d, J=2.3 Hz, 1H), 5.25 (d, J=16.3 Hz, 1H), 3.78 (m, 1H), 3.70 (s, 3H), 3.68 (d, J=16.3 Hz, 1H), 3.03 (s, 3H), 3.00-2.80 (m, 3H), 2.40 (dd, J=16.7, 5.3 Hz, 1H).

Workup

  1. filtrationthe mixture was filtered
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-6642288daba24ca89fb5649fa88c4f09
Source dataset
uspto-grants-2002_10
Patent number
US06458784B1

Reaction notes

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