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

HRID 1015559ノート

反応式

HRID 1015559 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6212Chloroform溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5fb4344bbf1e4bc58428c68708c3e7ad
出典データセット
uspto-grants-2011_07
特許番号
US07985759B2

反応ノート

読み込み中…