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

HRID 1075442

반응식

HRID 1075442 반응식
C(N[CH:5]([CH3:7])[CH3:6])(C)C.[Li][CH2:9]CCC.C([O:17][C:18](=[O:20])[CH3:19])CCC.[N:21]12[CH2:28][CH2:27][CH:24]([CH2:25][CH2:26]1)[C:23](=[O:29])[CH2:22]2>O1CCCC1.O>[C:5]([O:20][C:18](=[O:17])[CH2:19][C:23]1([OH:29])[CH:24]2[CH2:27][CH2:28][N:21]([CH2:26][CH2:25]2)[CH2:22]1)([CH3:6])([CH3:7])[CH3:9]

참가 물질

7

반응물 4

HCID 7912DiisopropylamineHCID 195073-QuinuclidinoneHCID 31272Butyl AcetateHCID 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 0° C. solution of diisopropylamine (6.7 ml) in tetrahydrofuran (THF) (20 ml) was added 2.3M nBuLi (20 ml). The reaction mixture was stirred for 40 minutes and then cooled to -78° C. To this mixture was added dropwise a solution of t butylacetate (6.4 ml) in 10 ml of THF and stirring continued for an additional 15 minutes. Quinuclidin-3-one (free base) (5.0 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 was added water (100 ml), 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 dried in vacuo to give 9.53 g of the subtitle compound as an off-white solid.

후처리

  1. stirringstirring
  2. waitcontinued 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. customdried in vacuo

출처 및 근거

ORD 기록
ord-2ba38bd6ef0b4c2ca5f565ac8defdc50
출처 데이터셋
uspto-grants-1999_05
특허 번호
US05902814

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