Acetic Acid → HCID 21064716, compound

HRID 1243791Notes

Reaction equation

HRID 1243791 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1)[OH:4].[C:11]([N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][C:19]1=O)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].C(O)(=O)C.[Na]>ClCCCl>[C:14]([O:13][C:11]([N:18]1[CH2:23][CH2:22][CH:21]([NH:1][CH2:2][CH:3]([OH:4])[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=2)[CH2:20][CH2:19]1)=[O:12])([CH3:17])([CH3:15])[CH3:16]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 38537792-(2-Amino-1-hydroxyethyl)pyridineHCID 5360545SodiumHCID 7577838tert-Butyl 2-oxopiperidine-1-carboxylate

Product 1

HCID 21064716HCID 21064716, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

2-Amino-1-pyridin-2-yl-ethanol (0.700 g, 5.07 mmol) and N-boc-piperidone (1.20 g, 5.90 mmol) was dissolved in 5 mL of 1,2-dichloroethane. Glacial acetic acid (0.40 mL, 7.0 mmol) was added followed by sodium tricaetoxyborohydride (2.00 g, 8.97 mmol). This mixture was stirred at room temperature under argon for 16 h. The solvent was removed in vacuo and the residue was purified by flash chromatography (silica gel 12 g, eluted with dichloromethane, MeOH and ammonium hydroxide 100 to 95:4.9:0.1) to give 4-(2-hydroxy-2-pyridin-2-yl-ethylamino)-piperidine-1-carboxylic acid tert-butyl ester as a brown oil (1.46 g, 90%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by flash chromatography (silica gel 12 g, eluted with dichloromethane, MeOH and ammonium hydroxide 100 to 95:4.9:0.1)

Sources & evidence

ORD record
ord-827736cc70874185a201f9e249407d46
Source dataset
uspto-grants-2006_10
Patent number
US07119102B2

Reaction notes

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