Sulfuric Acid → N-(3-hydroxy-5,7-dimethyl-1-adamantyl)acetamide

HRID 1167867ノート

反応式

HRID 1167867 の反応式
[OH:1]S(O)(=O)=O.[C:6]([NH:9][C:10]12[CH2:19][C:14]3([CH3:20])[CH2:15][CH:16]([CH2:18][C:12]([CH3:21])([CH2:13]3)[CH2:11]1)[CH2:17]2)(=[O:8])[CH3:7]>>[C:6]([NH:9][C:10]12[CH2:19][C:14]3([CH3:20])[CH2:15][C:16]([OH:1])([CH2:18][C:12]([CH3:21])([CH2:13]3)[CH2:11]1)[CH2:17]2)(=[O:8])[CH3:7]

参加物

3

反応物 2

HCID 1118Sulfuric AcidHCID 5276209N-(3,5-dimethyl-1-adamantyl)acetamide

生成物 1

HCID 2843103N-(3-hydroxy-5,7-dimethyl-1-adamantyl)acetamide

反応条件

温度
0 °C

実験手順

Fuming H2SO4 (3 mL) was added to 1-acetamido-3,5-dimethyladamantane (0.2 g) at 0° C. under nitrogen and the reaction mixture was stirred at 0° C. for 1 h. The reaction mixture was poured onto ice (10 g) and the product was extracted with ether (10 mL×4). The combined ether solution was washed with brine (10 mL) and water (10 mL). The solution was dried using sodium sulfate. The solvent was removed in vacuo and, after crystallization on standing, 70 mg of white product was obtained. Pure product was obtained by recrystallization in ether. 1H NMR (DMSO-d6, ppm): 7.30 (brs, 1 H, NH), 4.37 (brs, 1 H, OH), 1.72 (s, 3 H, COCH3), 1.65 (s, 2 H), 1.47 (s, 4 H), 1.24-1.14 (dd, 4 H, J=11.2, 23.9 Hz), 0.99 (s, 2 H), 0.82 (s, 6 H, 2×CH3). m.p. 194-195° C. Anal. (C14H23NO2), C. H. N.

後処理

  1. additionThe reaction mixture was poured onto ice (10 g)
  2. extractionthe product was extracted with ether (10 mL×4)
  3. washThe combined ether solution was washed with brine (10 mL) and water (10 mL)
  4. customThe solution was dried
  5. customThe solvent was removed in vacuo
  6. customafter crystallization

出典と根拠

ORDレコード
ord-f9f3448b52af46029ec7036b7052b2ad
出典データセット
uspto-grants-2003_09
特許番号
US06620845B2

反応ノート

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