Triethylamine → HCID 22875707, compound

HRID 2257992Notes

Reaction equation

HRID 2257992 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][C:24]([CH2:27][C:28](O)=[O:29])=[CH:23][CH:22]=1.CCN=C=NCCCN(C)C>C(Cl)Cl>[N:21]1[CH:26]=[CH:25][C:24]([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:23][CH:22]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 810974-Pyridineacetic acid hydrochlorideHCID 22875699(1S)-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane hydrochloride

Product 1

HCID 22875707HCID 22875707, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine 1.75 ml (12.6 mill) was added to a methylene chloride 20 ml solution of (1S)-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane hydrochloride 0.95 g (5.0 mill) and 4-pyridylacetic acid hydrochloride 0.96 g (5.5 mill) and stirred at 0° C. for 30 min. WSC 1.35 g (7.04 mill) was added thereto, then temperature of the reaction mixture was gradually changed to room temperature and stirred for 24 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-(4-pyridylacetyl)-1,8,8trimethyl-3-azabicyclo[3.2.1]octane. The concentrate was added to THF 30 ml solution of lithium aluminum hydride 0.39 g (10.3 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 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. Yield: 0.35 g (Yield 27.1%)

Workup

  1. customwas gradually changed to room temperature
  2. stirringstirred for 24 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-03414d70dafa4e77b859e5095cad03de
Source dataset
uspto-grants-1997_08
Patent number
US05658923

Reaction notes

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