3-(13-tert-Butoxycarbonylamino-tricyclo[8.2.1.03,8]trideca-3(8),4,6-trien-5-yl)-acrylic acid methyl ester → 3-(13-tert-Butoxycarbonylamino-tricyclo-[8.2.1.03,8]trideca-3(8),4,6-trien-5-yl)-propionic acid methyl ester

HRID 722144Notes

Reaction equation

HRID 722144 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH:4]=[CH:5][C:6]1[CH:17]=[CH:16][C:15]2[CH2:14][CH:13]3[CH:18]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:10]([CH2:11][CH2:12]3)[CH2:9][C:8]=2[CH:7]=1.[H][H]>C(O)C.[OH-].[OH-].[Pd+2]>[CH3:1][O:2][C:3](=[O:27])[CH2:4][CH2:5][C:6]1[CH:17]=[CH:16][C:15]2[CH2:14][CH:13]3[CH:18]([NH:19][C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH:10]([CH2:11][CH2:12]3)[CH2:9][C:8]=2[CH:7]=1

Participants

5

Reactant 2

HCID 696662713-(13-tert-Butoxycarbonylamino-tricyclo[8.2.1.03,8]trideca-3(8),4,6-trien-5-yl)-acrylic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 696664593-(13-tert-Butoxycarbonylamino-tricyclo-[8.2.1.03,8]trideca-3(8),4,6-trien-5-yl)-propionic acid methyl esterYield 94.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

3-(13-tert-Butoxycarbonylamino-tricyclo[8.2.1.03,8]trideca-3(8),4,6-trien-5-yl)-acrylic acid methyl ester (300 mg, 0.809 mmol, prepared in Example 32 Step 3) and 20% palladium hydroxide on carbon (30 mg) in ethanol (30 ml) were stirred under 1 atm. of hydrogen at room temperature for 18 hours. The mixture was filtered through Celite and the filtrate concentrated to give a colourless oil 285 mg (94%). 1H NMR (CDCl3, 400 MHz) δ 7.00 (1H, d, J=8.2 Hz), 6.90 (2H, m), 4.97 (1H, m), 4.03 (1H, m), 3.67 (3H, s), 2.99 (2H, m), 2.89 (2H, m), 2.55–2.62 (4H, m), 2.48 (2H, m), 1.71 (2H, m), 1.47 (9H, s), 1.19 (2H, m).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-c0cb8351b3b949cbbf8065547eeba788
Source dataset
uspto-grants-2006_11
Patent number
US07138400B2

Reaction notes

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