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

HRID 49599

反応式

HRID 49599 の反応式
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]

参加物

7

反応物 4

HCID 7912DiisopropylamineHCID 10908tert-Butyl acetateHCID 195073-QuinuclidinoneHCID 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 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.

後処理

  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

出典と根拠

ORDレコード
ord-07a09ec3323641eda1bbfbc6cab93271
出典データセット
uspto-grants-2004_03
特許番号
US06706878B2

関連ノート

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