Hexane → HCID 21942244, compound

HRID 2216367Notes

Reaction equation

HRID 2216367 reaction equation
C[Si]([C:5]#[CH:6])(C)C.CCCCCC.C([Li])CCC.[N:18]12[CH2:27][CH:22]3[CH2:23][CH:24]([CH2:26][CH:20]([C:21]3=[O:28])[CH2:19]1)[CH2:25]2>O1CCCC1.CO>[C:22]([C:21]1([OH:28])[CH:20]2[CH2:19][N:18]3[CH2:25][CH:24]([CH2:5][CH:6]1[CH2:27]3)[CH2:26]2)#[CH:23]

Participants

7

Reactant 4

HCID 8058HexaneHCID 66111TrimethylsilylacetyleneHCID 1426421-Azatricyclo(3.3.1.1,3,7)decan-4-oneHCID 178418339Butyllithium

Product 1

HCID 21942244HCID 21942244, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 0.2 ml of trimethylsilylacetylene in 2 ml of tetrahydrofuran was added dropwise 0.64 ml of a 1.56 mol hexane solution of n-butyllithium in a dry ice-acetone bath. After stirring for 30 minutes, a solution of 50 mg of 1-azaadamantane-4-one in 1 ml of tetrahydrofuran was added dropwise to the mixture. After further stirring for 30 minutes, 1 ml of methanol was added to the mixture and the temperature was elevated to room temperature. The solvent was removed and water was added to the resulting solid. Crystals that remained were collected by filtration, to give 17 mg of the title compound.

Workup

  1. stirringAfter further stirring for 30 minutes
  2. customwas elevated to room temperature
  3. customThe solvent was removed
  4. additionwater was added to the resulting solid
  5. filtrationCrystals that remained were collected by filtration

Sources & evidence

ORD record
ord-7c0be272bcaf4c31bc85561c12181e4d
Source dataset
uspto-grants-2006_09
Patent number
US07112593B2

Reaction notes

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