Triethylamine → (1S)-3-(2-adamantylacetyl)-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane

HRID 2257979Notes

Reaction equation

HRID 2257979 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]12[CH2:29][CH:24]3[CH2:25][CH:26]([CH2:28][CH:22]([CH2:23]3)[CH:21]1[CH2:30][C:31](O)=[O:32])[CH2:27]2.CCN=C=NCCCN(C)C>C(Cl)Cl>[CH:20]12[CH2:29][CH:24]3[CH2:25][CH:26]([CH2:28][CH:22]([CH2:23]3)[CH:21]1[CH2:30][C:31]([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:32])[CH2:27]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 8709902-(Adamantan-2-yl)acetic acidHCID 22875699(1S)-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane hydrochloride

Product 1

HCID 67723817(1S)-3-(2-adamantylacetyl)-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine 0.69 ml was added in a methylene chloride 20 ml solution of (1S)-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane hydrochloride 0.78 g (4.1 mill), and stirred at 0° C. for 30 min. 2-adamantyl acetic acid 0.80 g (4.1 mill) and WSC 1.11 g (5.79 mill) were added therein, then temperature of the reaction mixture was gradually changed to room temperature and stirred for 23 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-(2-adamantylacetyl)-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane. The concentrate was added to THF 50 ml solution of lithium aluminum hydride 0.47 g (12 mill) and refluxed for 2 hours. The reaction mixture was cooled, 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=10:1-5:1) to obtain the product.

Workup

  1. customwas gradually changed to room temperature
  2. stirringstirred for 23 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-0893ba016683462faeb9fe5c80132a2f
Source dataset
uspto-grants-1997_08
Patent number
US05658923

Reaction notes

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