Acetic Acid → 4-Acetyl-1-azabicyclo[2.2.1]heptane

HRID 1587372Notes

Reaction equation

HRID 1587372 reaction equation
[N:1]12[CH2:7][C:4]([C:8](N(OC)C)=[O:9])([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.C[Li].[CH3:16]COCC.C(O)(=O)C>C1COCC1>[C:8]([C:4]12[CH2:7][N:1]([CH2:6][CH2:5]1)[CH2:2][CH2:3]2)(=[O:9])[CH3:16]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 3283Diethyl EtherHCID 156636181-Azabicyclo[2.2.1]hept-4-yl-N-methoxy-N-methyl carboxamideHCID 178418348HCID 178418348, compound

Product 1

HCID 106783104-Acetyl-1-azabicyclo[2.2.1]heptaneYield 68.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

1-Azabicyclo[2.2.1]hept-4-yl-N-methoxy-N-methyl carboxamide (D21) (10 g, 0.054 mole) was dissolved in dry THF (250 ml) under nitrogen cooled to -40° C. and treated with methyl lithium in ether (55 ml, 1 molar, 0.055 moles). The solution was allowed to warm to room temperature over a period of 1 h. Acetic acid (3.3 ml, leq) was added and the solution concentrated in vacuo to a gum. The residue was partitioned between chloroform and saturated aqueous potassium carbonate solution. The organic phase was separated, dried over sodium sulphate and concentrated in vacuo to a gum which was distilled in vacuo to afford 4-acetyl-1-azabicyclo[2.2.1]heptane (D22) (5.15 g, 0.037 mole, 68%).

Workup

  1. temperatureto warm to room temperature over a period of 1 h
  2. concentrationthe solution concentrated in vacuo to a gum
  3. customThe residue was partitioned between chloroform and saturated aqueous potassium carbonate solution
  4. customThe organic phase was separated
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo to a gum which
  7. distillationwas distilled in vacuo

Sources & evidence

ORD record
ord-a83bedb2d94b42de9867b49d3e5739af
Source dataset
uspto-grants-1993_06
Patent number
US05217975

Reaction notes

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