Sodium Bicarbonate → tert-Butyl 4-((2-(2,6-dichloropyridin-3-yl)ethyl)amino)piperidine-1-carboxylate

HRID 531036Notes

Reaction equation

HRID 531036 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:15][C:16]1[C:21]([CH2:22][CH:23]=O)=[CH:20][CH:19]=[C:18]([Cl:25])[N:17]=1.[NH2:26][CH:27]1[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]1.C(=O)(O)[O-].[Na+]>C1COCC1>[Cl:15][C:16]1[C:21]([CH2:22][CH2:23][NH:26][CH:27]2[CH2:28][CH2:29][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:31][CH2:32]2)=[CH:20][CH:19]=[C:18]([Cl:25])[N:17]=1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 12682914-Amino-1-Boc-piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 220381052-(2,6-Dichloropyridin-3-yl)acetaldehyde

Product 1

HCID 117992313tert-Butyl 4-((2-(2,6-dichloropyridin-3-yl)ethyl)amino)piperidine-1-carboxylateYield 94.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium triacetoxy borohydride (9.47 g) was added to a THF (60 mL) solution of (2,6-dichloropyridin-3-yl)acetaldehyde (5.66 g) and tert-butyl 4-aminopiperidine-1-carboxylate (7.16 g), and the mixture was stirred at room temperature for 1 hour. A saturated aqueous solution of sodium bicarbonate was added to the reaction mixture, followed by extraction with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/methanol) to obtain the title compound (10.5 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/methanol)

Sources & evidence

ORD record
ord-c6ddfd0dc83d41579a48b075125c0d08
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

Loading…