Triethylamine → HCID 22875708, compound

HRID 2257983Notes

Reaction equation

HRID 2257983 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.CCN=C=NCCCN(C)C.[OH:31][C:32]12[CH2:41][CH:36]3[CH2:37][CH:38]([CH2:40][CH:34]([CH:35]3[CH2:42][C:43](O)=[O:44])[CH2:33]1)[CH2:39]2>C(Cl)Cl>[OH:31][C:32]12[CH2:41][CH:36]3[CH2:37][CH:38]([CH2:40][CH:34]([CH:35]3[CH2:42][C:43]([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:44])[CH2:33]1)[CH2:39]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 22923629HCID 22923629, compound

Product 1

HCID 22875708HCID 22875708, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine 0.38 ml was added to a methylene chloride 15 ml solution of (1S)-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane hydrochloride 0.44 g, and stirred at 0° C. for 30 min. WSC 0.53 g and 5-hydroxy-2-adamantyl acetic acid 0.44 g were added therein, then temperature of the reaction mixture was gradually changed to room temperature and stirred for 14.5 hours. The reaction mixture was washed with saturated 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-hydroxy-2-adamantyl acetyl)-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane. The concentrate was added to THF 30 ml solution of lithium aluminum hydride 95.5 mg and refluxed under heating for 1.5 hours. The reaction mixture was cooled, then added water, and removed the insoluble material 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. Yield: 556 mg (Yield 79%)

Workup

  1. customwas gradually changed to room temperature
  2. stirringstirred for 14.5 hours
  3. washThe reaction mixture was washed with saturated 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-e1e76f5ff21b4f8a96f2f1a48bb2166f
Source dataset
uspto-grants-1997_08
Patent number
US05658923

Reaction notes

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