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

HRID 2053055Notes

Reaction equation

HRID 2053055 reaction equation
[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]

Participants

3

Reactant 2

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

Product 1

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

Conditions

Temperature
0 °C

Procedure

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, 1H, OH), 1.72 (s, 3H, COCH3), 1.65 (s, 2H), 1.47 (s, 4H), 1.24-1.14 (dd, 4H, J=11.2, 23.9 Hz), 0.99 (s, 2H), 0.82 (s, 6H, 2×CH3). m.p. 194-195° C. Anal. (C14H23NO2), C. H. N.

Workup

  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

Sources & evidence

ORD record
ord-b932317c5a454de4ac535e680491fede
Source dataset
uspto-grants-2008_02
Patent number
US07326730B2

Reaction notes

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