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

HRID 1075442

反応式

HRID 1075442 の反応式
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]

参加物

7

反応物 4

HCID 7912DiisopropylamineHCID 195073-QuinuclidinoneHCID 31272Butyl AcetateHCID 178418339Butyllithium

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2ba38bd6ef0b4c2ca5f565ac8defdc50
出典データセット
uspto-grants-1999_05
特許番号
US05902814

関連ノート

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