Ethanol → HCID 67385071, compound

HRID 2360982Notes

Reaction equation

HRID 2360982 reaction equation
[C:1]([O:5][C:6](=[O:42])[NH:7][CH:8]([CH2:36][C:37]1[S:38][CH:39]=[CH:40][CH:41]=1)[C:9]([N:11]1[CH2:16][CH2:15][C:14]([C:27](=[O:35])[NH:28][CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=2)[CH2:13][CH2:12]1)=[O:10])([CH3:4])([CH3:3])[CH3:2].C(O)C.[H][H]>O1CCCC1.[Pd]>[C:1]([O:5][C:6](=[O:42])[NH:7][C@@H:8]([CH2:36][C:37]1[S:38][CH:39]=[CH:40][CH:41]=1)[C:9]([N:11]1[CH2:12][CH2:13][C:14]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([NH2:24])=[CH:22][CH:23]=2)([C:27](=[O:35])[NH:28][CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)[CH2:15][CH2:16]1)=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 702EthanolHCID 67384978HCID 67384978, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67385071HCID 67385071, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {2-[4-Cyclohexylcarbamoyl-4-(4-nitro-benzyl)-piperidin-1-yl]-2-oxo-1-thiophen-2-ylmethyl-ethyl}-carbamic acid tert-butyl ester (9.77 mmol; 5.85 g) (prepared as in Example 1, substituting 4-nitrobenzylbromide for 4-biphenylmethyl bromide and cyclohexylamine for cyclohexylmethylamine), in tetrahydrofuran (20 mL) and ethanol (40 mL) was added 10% palladium on carbon (2 g), and the resulting mixture was hydrogenated under 50 psi of hydrogen pressure overnight at room temperature. The catalyst was removed via filtration, and the filtrate was evaporated to yield (S)-{2-[4-(4-aminobenzyl)-4-cyclohexylcarbamoyl-piperidin-1-yl]-2-oxo-1-thiophen-2-ylmethyl-ethyl}-carbamic acid tert-butyl ester. MS (ESI) m/z 569.40 [M+H]+.

Workup

  1. customThe catalyst was removed via filtration
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-7d46f6f4cbba4f47aa7635b2df09b7e1
Source dataset
uspto-grants-2014_04
Patent number
US08686152B2

Reaction notes

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