Water → 2-(Tert-butoxycarbonyl)-2-azatricyclo[3.3.1.13,7]decane-5-carboxylic acid

HRID 623982ノート

反応式

HRID 623982 の反応式
[CH:1]12[CH2:10][C:5]3([C:11]([O:13]C)=[O:12])[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[N:2]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:8]2.C1COCC1.O.[Li+].[OH-]>CO>[C:18]([O:17][C:15]([N:2]1[CH:3]2[CH2:9][CH:7]3[CH2:6][C:5]([C:11]([OH:13])=[O:12])([CH2:10][CH:1]1[CH2:8]3)[CH2:4]2)=[O:16])([CH3:21])([CH3:19])[CH3:20]

参加物

6

反応物 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 897205112-Tert-butyl 5-methyl 2-azatricyclo[3.3.1.13,7]decane-2,5-dicarboxylate

生成物 1

HCID 897147462-(Tert-butoxycarbonyl)-2-azatricyclo[3.3.1.13,7]decane-5-carboxylic acid

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

To a 0° C. cooled stirred solution of 2-tert-butyl 5-methyl 2-azatricyclo[3.3.1.13,7]decane-2,5-dicarboxylate, intermediate-9 (0.16 g, 0.5 mmol) dissolved in methanol (3 ml), THF (1 ml) and water (1 ml), LiOH (50 mg, 2 mmol) was added and the resulting reaction mass was stirred at room temperature for 6 hrs. Upon completion of the reaction (reaction monitored by TLC), the solvent present in the reaction mixture was completely removed under vacuum and the crude residue was acidified with saturated citric acid solution and extracted with ethyl acetate (3×15 ml). The organic layer was then washed with brine solution and dried over sodium sulfate and was finally concentrated under vacuum to get intermediate-10 as an oily mass, 0.16 g (95%).

後処理

  1. customthe resulting reaction mass
  2. customUpon completion of the reaction (reaction monitored by TLC)
  3. customthe solvent present in the reaction mixture was completely removed under vacuum
  4. extractionextracted with ethyl acetate (3×15 ml)
  5. washThe organic layer was then washed with brine solution
  6. dry with materialdried over sodium sulfate
  7. concentrationwas finally concentrated under vacuum
  8. customto get intermediate-10 as an oily mass, 0.16 g (95%)

出典と根拠

ORDレコード
ord-39bbc7b12f444aab8ea0ad1ba00415ba
出典データセット
uspto-grants-2016_04
特許番号
US09303016B2

反応ノート

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