Hexane → 3-[3-Hydroxy-3-(4-methoxyphenyl)-3-(2-thienyl)-1-propynyl]quinuclidin-3-ol

HRID 900775노트

반응식

HRID 900775 반응식
[Li]CCCC.CCCCCC.[C:12]([C:14]1([OH:22])[CH:19]2[CH2:20][CH2:21][N:16]([CH2:17][CH2:18]2)[CH2:15]1)#[CH:13].[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]([C:33]2[S:34][CH:35]=[CH:36][CH:37]=2)=[O:32])=[CH:27][CH:26]=1>C1COCC1>[OH:32][C:31]([C:28]1[CH:29]=[CH:30][C:25]([O:24][CH3:23])=[CH:26][CH:27]=1)([C:33]1[S:34][CH:35]=[CH:36][CH:37]=1)[C:13]#[C:12][C:14]1([OH:22])[CH:19]2[CH2:20][CH2:21][N:16]([CH2:17][CH2:18]2)[CH2:15]1

참가 물질

6

반응물 4

HCID 8058HexaneHCID 77812(4-Methoxyphenyl)-2-thienylmethanoneHCID 36135173-Ethynyl-1-azabicyclo[2.2.2]octan-3-olHCID 178418339Butyllithium

생성물 1

HCID 692922983-[3-Hydroxy-3-(4-methoxyphenyl)-3-(2-thienyl)-1-propynyl]quinuclidin-3-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A 1.6 N solution of BuLi in hexane (1.12 ml, 1.79 mmol) was added dropwise to a solution of 3-ethynyl-1-azabicyclo[2.2.2]octan-3-ol 47 (123 mg, 0.81 mmol) in THF (5 ml) at room temperature. After stirring for 30 minutes, (4-methoxyphenyl)(2-thienyl)methanone (231 mg, 1.06 mmol, commercial) in THF (1 ml) was added slowly. After 2 hours, the reaction was quenched by addition of saturated aqueous NH4Cl solution and diluted with AcOEt. The organic phase was washed with brine, dried over Na2SO4 and evaporated. The yellowish oil was purified by chromatography on silica gel (CH2Cl2/MeOH 85/15) and 3-[3-hydroxy-3-(4-methoxyphenyl)-3-(2-thienyl)-1-propynyl]quinuclidin-3-ol 152 was obtained as a white solid (41 mg, 14%, mixture of diastereomers).

후처리

  1. waitAfter 2 hours
  2. customthe reaction was quenched by addition of saturated aqueous NH4Cl solution
  3. additiondiluted with AcOEt
  4. washThe organic phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe yellowish oil was purified by chromatography on silica gel (CH2Cl2/MeOH 85/15)

출처 및 근거

ORD 기록
ord-34f0e29cbfac46a5b353d9f10fb802e7
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07361668B2

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