1-Adamantanol → HCID 13675783, compound

HRID 1993932Notes

Reaction equation

HRID 1993932 reaction equation
[CH3:1][C:2]1[NH:6][NH:5][C:4](=[O:7])[CH:3]=1.[C:8]12(O)[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2>>[C:8]12([C:3]3[C:4](=[O:7])[NH:5][NH:6][C:2]=3[CH3:1])[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2

Participants

3

Reactant 2

HCID 641521-AdamantanolHCID 3197713H-Pyrazol-3-one, 2,4-dihydro-5-methyl-

Product 1

HCID 13675783HCID 13675783, compoundYield 107.7%

Conditions

Temperature
0 °C

Procedure

A suspension of 5-methyl-1,2-dihydro-pyrazol-3-one (4.0 g) and adamantan-1-ol (5.6 g) in a round bottom flask was cooled to 0° C. with an ice/water bath. To the cooled suspension was added borontrifluoride ethyl etherate (9.2 mL) over 10 minutes. The reaction mixture was then allowed to warm up to ambient temperature and stirred for 24 hours. The suspension was then re-cooled to 0° C. and quenched with 50% KOH solution. The mixture was then acidified with 2 N aqueous HCl solution and diluted with EtOAc. The resultant white precipitate was then collected by filtration and the solid was washed with ether. The white solid was dried in a dessicator to give the desired 4-adamantan-1-yl-5-methyl-1,2-dihydro-pyrazol-3-one (9.2 g) as a white solid. MS (ESI+): 233.3 [M+H]+).

Workup

  1. temperatureto warm up to ambient temperature
  2. temperatureThe suspension was then re-cooled to 0° C.
  3. customquenched with 50% KOH solution
  4. additiondiluted with EtOAc
  5. filtrationThe resultant white precipitate was then collected by filtration
  6. washthe solid was washed with ether
  7. customThe white solid was dried in a dessicator

Sources & evidence

ORD record
ord-c57fcd4f65884e478bb968a15efe1821
Source dataset
uspto-grants-2010_01
Patent number
US07652057B2

Reaction notes

Loading…