Triethylamine → HCID 67723149, compound

HRID 2257985Notes

Reaction equation

HRID 2257985 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.[C:20]1([C:26]23[CH2:35][CH:30]4[CH2:31][CH:32]([CH2:34][CH:28]([CH:29]4[CH2:36][C:37](O)=[O:38])[CH2:27]2)[CH2:33]3)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CCN=C=NCCCN(C)C>C(Cl)Cl>[C:20]1([C:26]23[CH2:27][CH:28]4[CH2:34][CH:32]([CH2:31][CH:30]([CH:29]4[CH2:36][C:37]([N:12]4[CH2:13][CH:14]5[C:17]([CH3:19])([CH3:18])[C@:10]([CH3:9])([CH2:16][CH2:15]5)[CH2:11]4)=[O:38])[CH2:35]2)[CH2:33]3)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 22875699(1S)-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane hydrochlorideHCID 22923630HCID 22923630, compound

Product 1

HCID 67723149HCID 67723149, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine 14.0 gl was added to a methylene chloride 1 ml solution of (1S)-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane hydrochloride 15.9 mg and stirred at O@C for 30 min. 5-phenyl-2-adamantyl acetic acid 22.6 mg and WSC 19.3 mg were added therein, then temperature of the reaction mixture was gradually changed to room temperature and stirred for 64 hours. The reaction mixture was washed with saturated aqueous sodium chloride solution and dried by anhydrous sodium sulfate. After filtering the drying agent, the filtrate was concentrated in vacuo to obtain crude (1S)-3-(5-phenyl-2-adamantylacetyl)1,8,8-trimethyl-3-azabicyclo[3.2.1]octane. The concentrate was added to THF 3 ml solution of lithium aluminum hydride 3.8 mg and refluxed under heating for 1.5 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 20:1) to obtain the product. Yield: 7.0 mg (Yield 21%)

Workup

  1. customwas gradually changed to room temperature
  2. stirringstirred for 64 hours
  3. washThe reaction mixture was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried by anhydrous sodium sulfate
  5. filtrationAfter filtering the drying agent
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-84ffc8b0e52a4fc7880407aa7a0bea8a
Source dataset
uspto-grants-1997_08
Patent number
US05658923

Reaction notes

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