Tetrahydrofuran → 3-(3,3-Diphenyl-1-butynyl)quinuclidin-3-ol

HRID 900778노트

반응식

HRID 900778 반응식
[CH3:1][C:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:3]#[CH:4].[Li]CCCC.CCCCCC.[N:28]12[CH2:35][CH2:34][CH:31]([CH2:32][CH2:33]1)[CH2:30][C:29]2=O.C1C[O:40]CC1>CCOCC>[C:11]1([C:2]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)([CH3:1])[C:3]#[C:4][C:30]2([OH:40])[CH:31]3[CH2:34][CH2:35][N:28]([CH2:33][CH2:32]3)[CH2:29]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

참가 물질

7

반응물 5

HCID 8028Tetrahydrofuran2회HCID 8058HexaneHCID 5661192-QuinuclidoneHCID 10929756(1-Methyl-1-phenyl-2-propynyl)benzeneHCID 178418339Butyllithium

생성물 1

HCID 99242603-(3,3-Diphenyl-1-butynyl)quinuclidin-3-ol수율 61%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

(1-methyl-1-phenyl-2-propynyl)benzene (Dehmlow E., Tetrahedron Lett. (1971), 563-566) (380 mg, 1.84 mmol.) in THF (10 ml) at −78° C. was treated with a 1.6 N solution of BuLi in hexane (1.21 ml, 1.94 mmol). After 30 minutes, at the same temperature, a solution of quinuclidinone (300 mg, 2.4 mmol) in THF (5 ml) was added dropwise. After 1 hour, the reaction was left at room temperature for 12 hours. The mixture was then diluted with ether and washed with water (twice) and brine. The organic phase was dried over MgSO4 and evaporated to dryness. Chromatography on silica gel (elution: CH2Cl2/EtOH/NH4OH 90/10/0.1) gave 3-(3,3-diphenyl-1-butynyl)quinuclidin-3-ol 195 as a white solid (380 mg, 61%). This compound was used as such in the next step.

후처리

  1. waitAfter 1 hour
  2. waitthe reaction was left at room temperature for 12 hours
  3. washwashed with water (twice) and brine
  4. dry with materialThe organic phase was dried over MgSO4
  5. customevaporated to dryness

출처 및 근거

ORD 기록
ord-62c944c1be1d4d4bb9cb042cbaa33ff7
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07361668B2

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