Hexane → HCID 15196231, compound

HRID 1736380Notes

Reaction equation

HRID 1736380 reaction equation
Br[C:2]1[CH:6]=[CH:5][O:4][CH:3]=1.C([Li])CCC.CCCCCC.[N:18]12[CH2:25][CH2:24][CH:21]([CH2:22][CH2:23]1)[C:20](=[O:26])[CH2:19]2.C(=O)([O-])[O-].[K+].[K+]>CCOCC>[O:4]1[CH:5]=[CH:6][C:2]([C:20]2([OH:26])[CH:21]3[CH2:24][CH2:25][N:18]([CH2:23][CH2:22]3)[CH2:19]2)=[CH:3]1

Participants

7

Reactant 5

HCID 8058HexaneHCID 11430Potassium CarbonateHCID 195073-QuinuclidinoneHCID 891643-BromofuranHCID 178418339Butyllithium

Product 1

HCID 15196231HCID 15196231, compoundYield 26.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A stirred solution of 3-bromofuran (5.0 g of technical grade, 0.034 mole) in dry ether (130 ml) at -60° C. under nitrogen was treated with 1.6M n-butyllithium in hexane (18.7 ml, 0.030 mole) and then stirred for 5 minutes. A solution of 1-azabicyclo[2.2.2]octan-3-one (3.37 g, 0.027 mole) in dry ether (10 ml) was added and the resulting mixture stirred for 40 minutes at -60° C., then allowed to warm to room temperature. The mixture was treated with potassium carbonate solution (100 ml) and extracted with ethyl acetate (2×100 ml). The combined extracts were dried (Na2SO4) and concentrated in vacuo to leave a yellow oil, which was chromatographed on basic alumina eluting with ethyl acetate. The pale yellow oil obtained crystallised on standing. This material was recrystallised from acetone to give the title compound (D20) as a white solid (1.40 g, 21%) m.p. 130°-133° C.

Workup

  1. stirringthe resulting mixture stirred for 40 minutes at -60° C.
  2. extractionextracted with ethyl acetate (2×100 ml)
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto leave a yellow oil, which
  6. customwas chromatographed on basic alumina eluting with ethyl acetate
  7. customThe pale yellow oil obtained
  8. customcrystallised
  9. customThis material was recrystallised from acetone

Sources & evidence

ORD record
ord-0437f83600954d1693916baebc3c28fb
Source dataset
uspto-grants-1996_07
Patent number
US05541194

Reaction notes

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