Sodium Bicarbonate → HCID 59714861, compound

HRID 2223882Notes

Reaction equation

HRID 2223882 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][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.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][CH2:27][C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)=[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 2724942TriacetoxyborohydrideHCID 230210485-Methyl-N-(piperidin-4-YL)pyridin-2-amineHCID 23021060HCID 23021060, compound

Product 1

HCID 59714861HCID 59714861, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(piperidin-4-ylamino)-5-methylpyridine (277 mg) and benzyl 1-(2-oxoethyl)cyclohexanecarboxylate (360 mg) in tetrahydrofuran (15 mL) was added acetic acid (207 mg) and triacetoxyborohydride (731 mg) at room temperature. After stiring the solution for 18 hours, saturated aqueous sodium bicarbonate solution was added thereto and it was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and then, concentrated under reduced pressure. The resulting residue was purified by chromatography (NH silica gel, hexane:ethyl acetate=2:1) to give the title compound (520 mg).

Workup

  1. customfor 18 hours
  2. extractionit was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by chromatography (NH silica gel, hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-72e096d42f3e4677b307e42aa378eef8
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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