Ethyl Acetate → HCID 59752320, compound

HRID 73188Notes

Reaction equation

HRID 73188 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([N:17]([C:27]2[CH:31]=[C:30]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[S:29][C:28]=2[C:38]([O:40][CH3:41])=[O:39])[C:18]([CH:20]2[CH2:25][CH2:24][CH:23]([CH3:26])[CH2:22][CH2:21]2)=[O:19])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.C(OCC)(=O)C>[Pd].CO>[CH3:41][O:40][C:38]([C:28]1[S:29][C:30]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)=[CH:31][C:27]=1[N:17]([C:18]([CH:20]1[CH2:21][CH2:22][CH:23]([CH3:26])[CH2:24][CH2:25]1)=[O:19])[CH:14]1[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]1)=[O:39]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 597523304-[(2-Methoxycarbonyl-5-phenyl-thiophen-3-yl)-(4-methyl-cyclohexanecarbonyl)-amino]-piperidine-1-carboxylic acid benzyl ester

Product 1

HCID 59752320HCID 59752320, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-[(2-Methoxycarbonyl-5-phenyl-thiophen-3-yl)-(4-methyl-cyclohexanecarbonyl)-amino]-piperidine-1-carboxylic acid benzyl ester (506 mg, 0.88 mmol) in a 6:1 mixture of ethyl acetate and methanol (7 ml) was added the 10% palladium on charcoal (103 mg, 0.097 mmol). The resulting reaction mixture was placed under H2 atmosphere (25 psi), stirred at room temperature for 3 days, and then filtered on celite and evaporated to dryness. The crude product was purified by flash chromatography (100/90/16/1 CH2Cl2/CHCl3/MeOH/Et3N) to give 287 mg (74%) of 3-[(4-Methyl-cyclohexanecarbonyl)-piperidin-4-yl-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester.

Workup

  1. customThe resulting reaction mixture
  2. filtrationfiltered on celite
  3. customevaporated to dryness
  4. customThe crude product was purified by flash chromatography (100/90/16/1 CH2Cl2/CHCl3/MeOH/Et3N)

Sources & evidence

ORD record
ord-8c65d26033b14e9da2245482752070a7
Source dataset
uspto-grants-2014_09
Patent number
US08829030B2

Reaction notes

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