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

HRID 900780

반응식

HRID 900780 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-40 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-0b1e9707afbd4f38ac9c6a2f3da37b6d
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07361668B2

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