Triethylamine → HCID 57095462, compound

HRID 2257990Notes

Reaction equation

HRID 2257990 reaction equation
[CH2:1]([N:3](CC)[CH2:4]C)C.Cl.C[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].Cl.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][C:25]([OH:27])=O.[CH3:28]CN=C=NCCCN(C)C>C(Cl)Cl>[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[CH2:24][C:25]([N:3]1[CH2:4][CH:14]2[C:15]([CH3:16])([CH3:28])[C@:11]([CH3:10])([CH2:12][CH2:13]2)[CH2:1]1)=[O:27]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 853172-Pyridineacetic acid, hydrochloride (1:1)HCID 22221522HCID 22221522, compound

Product 1

HCID 57095462HCID 57095462, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine 3.50 ml (25.1 mill) was added to a methylene chloride 40 ml solution of (1S)-1,8,8-trimethyl-3-azabicyclo[3.2.]octane hydrochloride 1.9 og (10.0 mill) and 2-pyridylacetic acid hydrochloride 1.92 g (11.6 mill) and stirred at 0° C. for 30 min. WSC 2.70 g (14.1 mm) was added therein, then temperature of the reaction mixture was gradually changed to room temperature and stirred for 48 hours. The reaction mixture was washed with saturated aqueous sodium chloride solution and dried by anhydrous sodium sulfate. After the drying agent was removed by filtration, the filtrate was concentrated in vacuo to obtain crude (1S)-3-(2-pyridylacetyl)1,8,8-trimethyl-3-azabicyclo[3.2.1]octane. The concentrate was added to THF 60 ml solution of lithium aluminum hydride 0.77 g (20.3 mill) and refluxed under heating for 1 hour. The reaction mixture was cooled, then water was added thereto and the insoluble material was removed by filtration. The filtrate was concentrated in vacuo. The thus obtained residue was purified by means of silica gel column chromatography (Wako gel, C200,chloroform: acetone =10:1) to obtain the product as orange colored oily material.

Workup

  1. customwas gradually changed to room temperature
  2. washThe reaction mixture was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried by anhydrous sodium sulfate
  4. customAfter the drying agent was removed by filtration
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c1ee45ba0089402c8ce5db38cda2d64f
Source dataset
uspto-grants-1997_08
Patent number
US05658923

Reaction notes

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