Boron trifluoride etherate → (3R)-3-(3-cyclohexyl-3-phenyl-1-propynyl)-1-azabicyclo[2.2.2]oct-3-yl methyl ether

HRID 900780ノート

反応式

HRID 900780 の反応式
[CH:1]1([C:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(O)[C:8]#[C:9][C@:10]2([O:18][CH3:19])[CH:15]3[CH2:16][CH2:17][N:12]([CH2:13][CH2:14]3)[CH2:11]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[SiH](CC)(CC)CC.B(F)(F)F.CCOCC>C(Cl)Cl>[CH3:19][O:18][C@@:10]1([C:9]#[C:8][CH:7]([CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:15]2[CH2:16][CH2:17][N:12]([CH2:13][CH2:14]2)[CH2:11]1

参加物

5

反応物 3

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 444065731-cyclohexyl-3-((R)-3-methoxyquinuclidin-3-yl)-1-phenylprop-2-yn-1-ol

生成物 1

HCID 69290748(3R)-3-(3-cyclohexyl-3-phenyl-1-propynyl)-1-azabicyclo[2.2.2]oct-3-yl methyl ether収率 98.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-40 °C

実験手順

1-cyclohexyl-3-[(3R)-3-methoxy-1-azabicyclo[2.2.2]oct-3-yl]-1-phenyl-2-propyn-1-ol 201 (150 mg, 0.42 mmol) was dissolved under argon in CH2Cl2 (20 ml) and then cooled to −40° C. Neat Et3SiH (203 μL, 1.27 mmol) was added dropwise. After 5 minutes, neat BF3.OEt2 (376 μL, 1.27 mmol) was slowly added to the mixture. After 15 minutes, the reaction was slowly left to room temperature, then quenched with saturated aqueous K2CO3 solution after 45 minutes and diluted with ether. The organic phase was dried over Na2SO4 and evaporated to dryness to give (3R)-3-(3-cyclohexyl-3-phenyl-1-propynyl)-1-azabicyclo[2.2.2]oct-3-yl methyl ether 112 (mixture of diastereomers) as a colorless oil (140 mg, 97%).

後処理

  1. waitAfter 15 minutes
  2. waitthe reaction was slowly left to room temperature
  3. customquenched with saturated aqueous K2CO3 solution after 45 minutes
  4. additiondiluted with ether
  5. dry with materialThe organic phase was dried over Na2SO4
  6. customevaporated to dryness

出典と根拠

ORDレコード
ord-0b1e9707afbd4f38ac9c6a2f3da37b6d
出典データセット
uspto-grants-2008_04
特許番号
US07361668B2

反応ノート

読み込み中…