(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 407960Notes

Reaction equation

HRID 407960 reaction equation
C(OC(=O)[NH:10][C@H:11]1[CH2:16][CH2:15][CH2:14][N:13]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]3[N:28]=[CH:27][C:26]([CH2:29][CH3:30])=[CH:25][N:24]=3)[CH2:19][CH2:18]2)[C:12]1=[O:31])C1C=CC=CC=1>CO.[Pd]>[NH2:10][C@H:11]1[CH2:16][CH2:15][CH2:14][N:13]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]3[N:28]=[CH:27][C:26]([CH2:29][CH3:30])=[CH:25][N:24]=3)[CH2:19][CH2:18]2)[C:12]1=[O:31]

Participants

4

Reactant 1

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

Product 1

HCID 67470426(S)-3-amino-1'-(5-ethylpyrimidin-2-yl)-1,4'-bipiperidin-2-oneYield 18.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(S)-benzyl-1′-(5-ethylpyrimidin-2-yl)-2-oxo-[1,4′-bipiperidin]-3-ylcarbamate (2.176 g, 4.973 mmol) was dissolved in MeOH and 10% Pd/C (1 g) was added and stirred in a parr shaker at 30 psi overnight. The reaction was filtered through GF/F paper and separated on the reverse phase Horizon system to give (S)-3-amino-1′-(5-ethylpyrimidin-2-yl)-[1,4′-bipiperidin]-2-one (0.280 g, 0.9229 mmol, 18.56% yield) as a clear oil. Mass spectrum (apci) m/z=304.2 (M+H).

Workup

  1. filtrationThe reaction was filtered through GF/F paper
  2. customseparated on the reverse phase Horizon system

Sources & evidence

ORD record
ord-b9658f2d3aeb4e6dbea41e3597b35037
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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