Triethylamine → (1S)-3-cyclooctylacetyl-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane

HRID 2257977Notes

Reaction equation

HRID 2257977 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.[CH:20]1([CH2:28][C:29](O)=[O:30])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.CCN=C=NCCCN(C)C>C(Cl)Cl>[CH:20]1([CH2:28][C:29]([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:30])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 134114672-Cyclooctylacetic acidHCID 22875699(1S)-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane hydrochloride

Product 1

HCID 57242025(1S)-3-cyclooctylacetyl-1,8,8-trimethyl-3-azabicyclo[3.2.1]octaneYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine 0.24 ml was added in a methylene chloride 10 ml solution of (1S)-1,8,8-trimethyl-3-azabicyclo (3.2.1]octane hydrochloride 0.28 g, and stirred at 0° C. for 30 min. Cyclooctyl acetic acid 0.25 g and WSC 0.40 g were added therein, then temperature of the reaction mixture was gradually changed to room temperature and stirred for 21 hours. The reaction mixture was washed wits 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-cyclooctylacetyl-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane. The concentrate was added to THP 15 ml solution of lithium aluminum hydride 0.12 g and refluxed for 1 hour. The reaction mixture was cooled, then added water and filtered the insoluble material. 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. Yield: 0.26 g (Yield 61%)

Workup

  1. customwas gradually changed to room temperature
  2. stirringstirred for 21 hours
  3. washThe reaction mixture was washed wits 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-f006764d2fc649a48766c54e6caa80b4
Source dataset
uspto-grants-1997_08
Patent number
US05658923

Reaction notes

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