HCID 57939448, compound → HCID 57939424, compound

HRID 1436896Notes

Reaction equation

HRID 1436896 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][C@@H:14]([NH:17][C:18](=[O:21])[CH2:19][CH3:20])[CH2:13][C@@H:12]1[C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:23]=1[CH3:29])=O)C1C=CC=CC=1>C(O)C.[C].[Pd]>[F:28][C:25]1[CH:26]=[CH:27][C:22]([C@H:12]2[CH2:13][C@H:14]([NH:17][C:18](=[O:21])[CH2:19][CH3:20])[CH2:15][CH2:16][NH:11]2)=[C:23]([CH3:29])[CH:24]=1

Participants

4

Reactant 1

HCID 57939448HCID 57939448, compound

Product 1

HCID 57939424HCID 57939424, compoundYield 67.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

In 17 ml of ethanol was dissolved 1.73 g of trans-1-benzyloxycarbonyl-2-(4-fluoro-2-methylphenyl)-4-propanoylaminopiperidine, and added thereto was 280 mg of palladium-carbon (moisture content of 50.9%), and the mixture was stirred under hydrogen atmosphere at room temperature for 3 hours. The reaction mixture was filtered through Celite, and ethanol was removed by distillation. The residue was purified by NH silica gel column chromatography (chloroform:hexane:ethyl acetate=5:5:2), to give 772 mg of trans-2-(4-fluoro-2-methylphenyl)-4-propanoylaminopiperidine as shown in Table 129 below.

Workup

  1. additionadded
  2. filtrationThe reaction mixture was filtered through Celite, and ethanol
  3. customwas removed by distillation
  4. customThe residue was purified by NH silica gel column chromatography (chloroform:hexane:ethyl acetate=5:5:2)

Sources & evidence

ORD record
ord-9a432e57b65d423c9ff3db420e7b370d
Source dataset
uspto-grants-2009_11
Patent number
US07619092B2

Reaction notes

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