Nitromethane → 7a-nitromethyl-2,3,5,6,7,7a-hexahydro-1H-pyrrolizine

HRID 704100

Reaction equation

HRID 704100 reaction equation
[N+:1]([CH3:4])([O-:3])=[O:2].Cl[CH2:6][CH2:7][CH2:8][C:9](=O)[CH2:10][CH2:11][CH2:12]Cl.[NH3:15].CO>>[N+:1]([CH2:4][C:9]12[CH2:10][CH2:11][CH2:12][N:15]1[CH2:6][CH2:7][CH2:8]2)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 6375NitromethaneHCID 2467491,7-Dichloro-heptan-4-oneHCID 21705897Ammonia methanol

Product 1

HCID 104873597a-nitromethyl-2,3,5,6,7,7a-hexahydro-1H-pyrrolizineYield 90%

Conditions

Temperature
20 °C

Procedure

To a solution of nitromethane (0.67 g, 11 mmol) in 0.3 ml of 16% NH3 /MeOH, 1,7-dichloro-4-heptanone (0.50 g, 2.7 mmol) was added dropwise at 20° C. The resulting solution was stirred for 24 hours at 20° C. under ammonia gas atmosphere. The reaction mixture was concentrated and 0.1N NaOH was added to the residue to extract with methylene chloride. The extract was dried over anhydrous sodium sulfate, concentrated and distilled in vacuo to afford 0.42 g of the desired compound (Yield: 90%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. addition0.1N NaOH was added to the residue
  3. extractionto extract with methylene chloride
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. distillationdistilled in vacuo

Sources & evidence

ORD record
ord-f3023006ff74463695d8ee852d5a6d51
Source dataset
uspto-grants-1991_01
Patent number
US04985569

Linked notes

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