Triethylamine → (1S)-3-(bicyclo[3.3.1]nonan-9-yl)acetyl-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane

HRID 2257981ノート

反応式

HRID 2257981 の反応式
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[CH:28]([CH2:29][C:30](O)=[O:31])[CH:24]([CH2:25][CH2:26][CH2:27]1)[CH2:23][CH2:22][CH2:21]2.CCN=C=NCCCN(C)C>C(Cl)Cl>[CH:24]12[CH:28]([CH2:29][C:30]([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:31])[CH:20]([CH2:27][CH2:26][CH2:25]1)[CH2:21][CH2:22][CH2:23]2

参加物

6

反応物 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 22875699(1S)-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane hydrochlorideHCID 229236192-(Bicyclo[3.3.1]nonan-9-yl)acetic acid

生成物 1

HCID 57153325(1S)-3-(bicyclo[3.3.1]nonan-9-yl)acetyl-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Triethylamine 0.12 ml was added in a methylene chloride 10 ml solution of (1S)-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane hydrochloride 100 mg and stirred at 0° C. for 30 min. 9-bicyclo[3.3.1]nonylacetic acid 97.0 mg and WSC 0.15 g were added therein, then temperature of the reaction mixture was gradually changed to room temperature and stirred for 19 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-(bicyclo[3.3.1]nonan-9-yl)acetyl-1,8,8-trimethyl-3-azabicyclo[3.2.1]octane. The concentrate was added to THF 10 ml solution of lithium aluminum hydride 41 mg and refluxed under heating for 1 hour. 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:acetone=10:1-5:1) to obtain the product.

後処理

  1. customwas gradually changed to room temperature
  2. stirringstirred for 19 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

出典と根拠

ORDレコード
ord-52d8b7b7e5a84061bcb8b216298c0f3c
出典データセット
uspto-grants-1997_08
特許番号
US05658923

反応ノート

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