Triethylamine → HCID 86751167, compound

HRID 2257986Notes

Reaction equation

HRID 2257986 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.[OH:20][CH:21]1[CH:28]2[CH2:29][CH:24]3[CH2:25][CH:26]([CH2:30][CH:22]1[CH:23]3[CH2:31][C:32](O)=[O:33])[CH2:27]2.CCN=C=NCCCN(C)C>C(Cl)Cl>[OH:20][CH:21]1[CH:28]2[CH2:29][CH:24]3[CH2:25][CH:26]([CH2:30][CH:22]1[CH:23]3[CH2:31][C:32]([N:12]1[CH2:13][CH:14]3[C:17]([CH3:19])([CH3:18])[C@:10]([CH3:9])([CH2:16][CH2:15]3)[CH2:11]1)=[O:33])[CH2:27]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 22923665HCID 22923665, compound

Product 1

HCID 86751167HCID 86751167, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine 0.23 ml was added to a methylene chloride 5 ml solution of (IS)-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane hydrochloride 0.26 g and stirred at O@C for 30 min. 4-hydroxy-2-adamantyl acetic acid 0.26 g and WSC 0.31 g were added therein, then temperature of the reaction mixture was gradually changed to room temperature and stirred for 25 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-(4-hydroxy-2-adamantylacetyl)1,8,8-trimethyl-3-azabicyclo[3.2.1]octane. The concentrate was added to THF 25 ml solution of lithium aluminum hydride 70.5 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 methanol=150:1) to obtain the product.

Workup

  1. customwas gradually changed to room temperature
  2. stirringstirred for 25 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-56606fa5da02461fbc02561d3c35eccf
Source dataset
uspto-grants-1997_08
Patent number
US05658923

Reaction notes

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