Triethylamine → HCID 54012185, compound

HRID 2257991Notes

Reaction equation

HRID 2257991 reaction equation
C(N(CC)CC)C.Cl.[CH3:9][C@@:10]12[C:17]([CH3:19])([CH3:18])[CH:14]([CH2:15][CH2:16]1)[CH2:13][NH:12][CH2:11]2.Cl.[N:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][C:28](O)=[O:29])[CH:22]=1.CCN=C=NCCCN(C)C>C(Cl)Cl>[N:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH2:27][C:28]([N:12]2[CH2:13][CH:14]3[C:17]([CH3:19])([CH3:18])[C@:10]([CH3:9])([CH2:16][CH2:15]3)[CH2:11]2)=[O:29])[CH:22]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27237243-Pyridineacetic acid, hydrochloride (1:1)HCID 22875699(1S)-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane hydrochloride

Product 1

HCID 54012185HCID 54012185, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine 3.20 ml (23.0 mill) was added to a methylene chloride 40 ml solution of (IS)-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane hydrochloride 1.74 g (9.18 mill) and 3-pyridylacetic acid hydrochloride 1.76 g (10.1 mill) and stirred at 0° C. for 30 min. WSC 2.47 g (12.9 mill) was added therein, then temperature of the reaction mixture was gradually changed to room temperature and stirred for 46 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 (IS)-3-(3-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 3 hours. The reaction mixture was cooled, then water was added thereto and the insoluble material was removed by filtration. The filtrate was concentrate in vacuo. The thus obtained residue was purified by means of silica gel column chromatography (Wako gel, C200, chloroform:acetone=10:1-5:1) to obtain the product as yellowish oily material.

Workup

  1. customwas gradually changed to room temperature
  2. stirringstirred for 46 hours
  3. washThe reaction mixture was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried by anhydrous sodium sulfate
  5. customAfter the drying agent was removed by filtration
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-23222435777241f699a3b48df05df679
Source dataset
uspto-grants-1997_08
Patent number
US05658923

Reaction notes

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