Diisopropylamine → (+/-)-3-(1,2-dihydro-1-hydroxy-2,2-dimethyl-1-acenaphthylenyl)-N,N-bis(1-methylethyl)-4-pyridinecarboxamide

HRID 2380567Notes

Reaction equation

HRID 2380567 reaction equation
CC(NC(C)C)C.C([Li])CCC.[CH3:13][CH:14]([N:16]([CH:25]([CH3:27])[CH3:26])[C:17]([C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1)=[O:18])[CH3:15].[CH3:28][C:29]1([CH3:42])[C:39]2[C:40]3[C:35]([CH:36]=[CH:37][CH:38]=2)=[CH:34][CH:33]=[CH:32][C:31]=3[C:30]1=[O:41]>O1CCCC1.O>[OH:41][C:30]1([C:20]2[CH:21]=[N:22][CH:23]=[CH:24][C:19]=2[C:17]([N:16]([CH:25]([CH3:27])[CH3:26])[CH:14]([CH3:13])[CH3:15])=[O:18])[C:31]2=[C:40]3[C:35](=[CH:34][CH:33]=[CH:32]2)[CH:36]=[CH:37][CH:38]=[C:39]3[C:29]1([CH3:42])[CH3:28]

Participants

7

Reactant 4

HCID 7912DiisopropylamineHCID 234345N,N-bis(propan-2-yl)pyridine-4-carboxamideHCID 6024932,2-Dimethyl-1-acenaphthenoneHCID 178418339Butyllithium

Product 1

HCID 18954651(+/-)-3-(1,2-dihydro-1-hydroxy-2,2-dimethyl-1-acenaphthylenyl)-N,N-bis(1-methylethyl)-4-pyridinecarboxamideYield 22%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-80 °C

Procedure

Preparation of: ##STR30## To a cooled (-80° C.) and stirred solution of 5.25 g of N-(1-methylethyl)-2-propanamine in 500 ml of dry tetrahydrofuran there were added 20 ml of butyl lithium (2.5M in hexane) and, after stirring for 1 hour at -80° C., 10.3 g of N,N-bis(1-methylethyl)-4-pyridinecarboxamide (prepared as described in Tetr. Lett. 21, 4739, 1980). Stirring at -80° C. was continued for 3 hours and then there were added 9.3 g of 2,2-dimethylacenaphthylen-1(2H)-one. The whole was stirred for 18 hours at room temperature and was then poured into water. The product was extracted with ether and the extract was dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 95:5). The eluent of the desired fraction was evaporated, yielding 4.2 g (20.9% ) of (±)-3-(1,2-dihydro-1-hydroxy-2,2-dimethyl-1-acenaphthylenyl)-N,N-bis(1-methylethyl)- 4-pyridinecarboxamide (comp. 5.006)

Workup

  1. customPreparation of: ##STR30## To
  2. stirringStirring at -80° C.
  3. waitwas continued for 3 hours
  4. stirringThe whole was stirred for 18 hours at room temperature
  5. extractionThe product was extracted with ether
  6. customthe extract was dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 95:5)
  10. customThe eluent of the desired fraction was evaporated

Sources & evidence

ORD record
ord-08a66fbb1f4e4323aeb1b23fba8c7334
Source dataset
uspto-grants-1994_11
Patent number
US05369084

Reaction notes

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