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

HRID 900778ノート

反応式

HRID 900778 の反応式
[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

参加物

7

反応物 5

HCID 8028Tetrahydrofuran2 回HCID 8058HexaneHCID 5661192-QuinuclidoneHCID 10929756(1-Methyl-1-phenyl-2-propynyl)benzeneHCID 178418339Butyllithium

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-62c944c1be1d4d4bb9cb042cbaa33ff7
出典データセット
uspto-grants-2008_04
特許番号
US07361668B2

反応ノート

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