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

HRID 623982노트

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HRID 623982 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

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온도
0 °C

실험 절차

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%).

후처리

  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%)

출처 및 근거

ORD 기록
ord-39bbc7b12f444aab8ea0ad1ba00415ba
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09303016B2

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