Sulfuric Acid → 1-Methoxytricyclo[3.3.1.03,7]nonan-3-amine

HRID 1015559노트

반응식

HRID 1015559 반응식
[CH3:1][O:2][C:3]12[CH2:11][CH:7]3[CH2:8][CH:9]([CH2:10]1)[C:5](C(O)=O)([CH2:6]3)[CH2:4]2.OS(O)(=O)=O.[N-:20]=[N+]=[N-].[Na+]>C(Cl)(Cl)Cl.O>[CH3:1][O:2][C:3]12[CH2:11][CH:7]3[CH2:8][CH:9]([CH2:10]1)[C:5]([NH2:20])([CH2:6]3)[CH2:4]2

참가 물질

6

반응물 3

HCID 1118Sulfuric AcidHCID 33557Sodium AzideHCID 673004371-Methoxytricyclo[3.3.1.03,7]nonane-3-carboxylic acid

생성물 1

HCID 670177601-Methoxytricyclo[3.3.1.03,7]nonan-3-amine수율 69%

시약·촉매·용매 2

HCID 962Water용매HCID 6212Chloroform용매

실험 절차

To the suspension of 1-methoxytricyclo[3.3.1.03,7]nonane-3-carboxylic acid obtained from step IV (0.39 g, 2.0 mmol) in CHCl3 (10 mL) was added conc. H2SO4 (1.0 mL, 20 mmol). Solid NaN3 (0.39 g, 6.0 mmol) was added in portions by keeping the reaction temperature below 40° C. After stirring at room temperature for 2 hrs, the reaction mixture was cooled to ice bath temperature, diluted with water and extracted with EtOAc. The aqueous layer was basified by adding 50% NaOH solution and extracted with CHCl3. The combined organic layer was washed with brine, dried over Na2SO4, and the solvent was removed under reduced pressure to obtain 1-methoxytricyclo[3.3.1.03,7]nonan-3-amine (0.23 g) in 69% yield. m/z (M+1) 168; 1H NMR (CDCl3) 300 MHz δ 3.27 (s, 3H), 2.40-2.34 (m, 1H), 2.16-2.08 (m, 1H), 1.97 (ddd, J=2.0, 6.8, 8.7 Hz, 1H), 1.92-1.53 (m, 7H), 1.51-1.38 (m, 2H).

후처리

  1. customthe reaction temperature below 40° C
  2. temperaturethe reaction mixture was cooled to ice bath temperature
  3. extractionextracted with EtOAc
  4. additionby adding 50% NaOH solution
  5. extractionextracted with CHCl3
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-5fb4344bbf1e4bc58428c68708c3e7ad
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07985759B2

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