Sodium Bicarbonate → Methyl 1-[2-[4-(5-methylpyridin-2-ylamino)piperidin-1-yl]ethyl]cyclohexanecarboxylate

HRID 2223879Notes

Reaction equation

HRID 2223879 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][N:9]=2)[CH2:3][CH2:2]1.O=[CH:16][CH2:17][C:18]1([C:24]([O:26][CH3:27])=[O:25])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1.C(O)(=O)C>[CH3:14][C:11]1[CH:12]=[CH:13][C:8]([NH:7][CH:4]2[CH2:5][CH2:6][N:1]([CH2:16][CH2:17][C:18]3([C:24]([O:26][CH3:27])=[O:25])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[CH2:2][CH2:3]2)=[N:9][CH:10]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 230210485-Methyl-N-(piperidin-4-YL)pyridin-2-amineHCID 23021124Methyl 1-(2-oxoethyl)cyclohexanecarboxylate

Product 1

HCID 59714834Methyl 1-[2-[4-(5-methylpyridin-2-ylamino)piperidin-1-yl]ethyl]cyclohexanecarboxylateYield 8.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(piperidin-4-ylamino)-5-methylpyridine (191 mg) and methyl 1-(2-oxoethyl)cyclohexanecarboxylate (250 mg) in tetrahydrofuran (10 mL) were added acetic acid (150 mg) and sodium triacetoxy borohydride (424 mg) at room temperature. The solution was stirred at room temperature for 20 hours. Saturated aqueous sodium bicarbonate solution was added to the solution, and it was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and then, concentrated under reduced pressure. The resulting residue was purified by chromatography [silica gel, ethyl acetate-methanol-aqueous ammonia (90:10:0.1)] to give the title compound (30 mg).

Workup

  1. extractionwas extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by chromatography [silica gel, ethyl acetate-methanol-aqueous ammonia (90:10:0.1)]

Sources & evidence

ORD record
ord-e9f5be7f489e4c85ac2eb6739530dd03
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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