Diisopropylamine → 2-(3-Hydroxy-1-azabicyclo[2.2.2]oct-3-yl)acetic acid t-butyl ester

HRID 49599

반응식

HRID 49599 반응식
C(NC(C)C)(C)C.C([Li])CCC.[C:13]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:15])[CH3:14].[N:21]12[CH2:28][CH2:27][CH:24]([CH2:25][CH2:26]1)[C:23](=[O:29])[CH2:22]2>O1CCCC1.O>[C:17]([O:16][C:13](=[O:15])[CH2:14][C:23]1([OH:29])[CH:24]2[CH2:27][CH2:28][N:21]([CH2:26][CH2:25]2)[CH2:22]1)([CH3:20])([CH3:19])[CH3:18]

참가 물질

7

반응물 4

HCID 7912DiisopropylamineHCID 10908tert-Butyl acetateHCID 195073-QuinuclidinoneHCID 178418339Butyllithium

생성물 1

HCID 453576912-(3-Hydroxy-1-azabicyclo[2.2.2]oct-3-yl)acetic acid t-butyl ester

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
-78 °C

실험 절차

To a solution of diisopropylamine (6.7 mL) in tetrahydrofuran (THF) (20 mL) at 0° C. was added n-butyllithium (2.3M in hexanes; 20 mL). The reaction mixture was stirred for 40 minutes and then cooled to −78° C. To this mixture a solution of t-butyl acetate (6.4 mL) in THF (10 mL) was added dropwise and stirring was continued for an additional 15 minutes. Quinuclidin-3-one (5 g) in THF (15 mL) was added to the mixture dropwise and the mixture was allowed to warm to 0° C. over 1 hour. To this solution water (100 mL) was added, the solution was extracted twice with chloroform and the combined extracts were washed once with brine. The resulting solution was dried over MgSO4, filtered, and evaporated in vacuo to give 9.53 g of the subtitle compound as an off-white solid.

후처리

  1. stirringstirring
  2. waitwas continued for an additional 15 minutes
  3. temperatureto warm to 0° C. over 1 hour
  4. extractionthe solution was extracted twice with chloroform
  5. washthe combined extracts were washed once with brine
  6. dry with materialThe resulting solution was dried over MgSO4
  7. filtrationfiltered
  8. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-07a09ec3323641eda1bbfbc6cab93271
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06706878B2

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