Methyl iodide → (S)-benzyl 1'-(5-ethylpyrimidin-2-yl)-2-oxo-1,4'-bipiperidin-3-yl(methyl)carbamate

HRID 407973Notes

Reaction equation

HRID 407973 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:22](=[O:31])[O:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:16]3=[O:32])[CH2:11][CH2:10]2)=[N:7][CH:8]=1)[CH3:2].[H-].[Na+].I[CH3:36]>CN(C=O)C>[CH2:1]([C:3]1[CH:8]=[N:7][C:6]([N:9]2[CH2:10][CH2:11][CH:12]([N:15]3[CH2:20][CH2:19][CH2:18][C@H:17]([N:21]([CH3:36])[C:22](=[O:31])[O:23][CH2:24][C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:16]3=[O:32])[CH2:13][CH2:14]2)=[N:5][CH:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86688094(S)-benzyl 1'-(5-ethylpyrimidin-2-yl)-2-oxo-1,4'-bipiperidin-3-ylcarbamate

Product 1

HCID 86688111(S)-benzyl 1'-(5-ethylpyrimidin-2-yl)-2-oxo-1,4'-bipiperidin-3-yl(methyl)carbamateYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-benzyl 1′-(5-ethylpyrimidin-2-yl)-2-oxo-1,4′-bipiperidin-3-ylcarbamate (Example 58, Steps A-B; 0.250 g, 0.571 mmol) was dissolved in DMF (5 mL). 60% NaH (0.0274 g, 0.686 mmol) was added and stirred for 5 minutes. Iodomethane (0.071 mL, 1.1 mmol) was added and stirred at ambient temperature overnight. The reaction was concentrated and purified over silica gel (25-100% EtOAc in hexanes) to afford (S)-benzyl 1′-(5-ethylpyrimidin-2-yl)-2-oxo-1,4′-bipiperidin-3-yl(methyl)carbamate (100 mg, 0.22 mmol, 39% yield).

Workup

  1. stirringstirred at ambient temperature overnight
  2. concentrationThe reaction was concentrated
  3. custompurified over silica gel (25-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-53b031b57863468382af6167205e9574
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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