(S)-benzyl 1'-(5-ethylpyrimidin-2-yl)-2-oxo-1,4'-bipiperidin-3-ylcarbamate → (S)-3-amino-1'-(5-ethylpyrimidin-2-yl)-1,4'-bipiperidin-2-one

HRID 407932Notes

Reaction equation

HRID 407932 reaction equation
[CH2:1]([C:3]1[CH:4]=[N:5][C:6]([N:9]2[CH2:14][CH2:13][CH:12]([N:15]3[CH2:20][CH2:19][CH2:18][C@H:17]([NH:21]C(=O)OCC4C=CC=CC=4)[C:16]3=[O:32])[CH2:11][CH2:10]2)=[N:7][CH:8]=1)[CH3:2].[H][H]>CCO.CCOC(C)=O.[Pd]>[NH2:21][C@H:17]1[CH2:18][CH2:19][CH2:20][N:15]([CH:12]2[CH2:13][CH2:14][N:9]([C:6]3[N:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][N:5]=3)[CH2:10][CH2:11]2)[C:16]1=[O:32]

Participants

5

Reactant 2

HCID 86688094(S)-benzyl 1'-(5-ethylpyrimidin-2-yl)-2-oxo-1,4'-bipiperidin-3-ylcarbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 67470426(S)-3-amino-1'-(5-ethylpyrimidin-2-yl)-1,4'-bipiperidin-2-oneYield 115.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

(S)-benzyl 1′-(5-ethylpyrimidin-2-yl)-2-oxo-1,4′-bipiperidin-3-ylcarbamate (275 mg, 0.629 mmol) was dissolved in 1:1 EtOH/EtOAc and 10% Pd/C (50 mg) was added, and the reaction was stirred under a balloon pressure of hydrogen for 1.5 hours. The reaction was filtered through celite and concentrated to afford crude (S)-3-amino-1′-(5-ethylpyrimidin-2-yl)-1,4′-bipiperidin-2-one (220 mg, 0.725 mmol, 115% yield) as an oil.

Workup

  1. additionwas added
  2. filtrationThe reaction was filtered through celite
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-976ac9c5ce8d42bf99aa480138d9aa08
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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