Triethylamine → HCID 86751166, compound

HRID 2257984Notes

Reaction equation

HRID 2257984 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.[CH3:20][O:21][C:22]12[CH2:31][CH:26]3[CH2:27][CH:28]([CH2:30][CH:24]([CH:25]3[CH2:32][C:33](O)=[O:34])[CH2:23]1)[CH2:29]2.CCN=C=NCCCN(C)C>C(Cl)Cl>[CH3:20][O:21][C:22]12[CH2:23][CH:24]3[CH2:30][CH:28]([CH2:27][CH:26]([CH:25]3[CH2:32][C:33]([N:12]3[CH2:13][CH:14]4[C:17]([CH3:19])([CH3:18])[C@:10]([CH3:9])([CH2:16][CH2:15]4)[CH2:11]3)=[O:34])[CH2:31]1)[CH2:29]2

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 22923634HCID 22923634, compound

Product 1

HCID 86751166HCID 86751166, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine 29.3 μl was added to a methylene chloride 1 ml solution of (IS)-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane hydrochloride 33.7 mg and stirred at 0° C. for 30 min. 5-methoxy-2-adamantyl acetic acid 36.2 mg and WSC 40.3 mg were added therein, then temperature of the reaction mixture was gradually changed to room temperature and stirred for 20.5 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 (IS)-3-(5-methoxy-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 7.4 mg and refluxed under heating for 1.5 hours. The reaction mixture was cooled, then water was added thereto and then 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=20:1-10:1) to obtain the product.

Workup

  1. customwas gradually changed to room temperature
  2. stirringstirred for 20.5 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-0430133ec62744efa92fb4317ad33991
Source dataset
uspto-grants-1997_08
Patent number
US05658923

Reaction notes

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