Methylamine → Ammonia

HRID 855599Notes

Reaction equation

HRID 855599 reaction equation
I[CH:2]1[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1.[CH3:13][NH2:14]>C(O)C>[NH3:4].[CH3:13][NH:14][CH:2]1[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 11000522Tert-butyl 3-iodoazetidine-1-carboxylate

Product 2

HCID 222AmmoniaHCID 23153172tert-Butyl 3-(methylamino)azetidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

tert-Butyl 3-iodoazetidine-1-carboxylate (EP 1176142, pg. 23, ex. 2 (i)) (2.0 g, 7.07 mmol) was added to 33% methylamine in ethanol (45 mL) and the reaction mixture heated in a sealed vessel at 100° C. for 24 hours. The reaction mixture was concentrated in vacuo and the residue partitioned between ethyl acetate and 1M aqueous sodium hydroxide. The organic layer was separated and washed with brine, dried over magnesium sulphate and concentrated in vacuo. The crude product was purified by column chromatography on silica gel eluting with dichloromethane:methanol:0.880 ammonia 96:3.5:0.5 to yield the title product.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue partitioned between ethyl acetate and 1M aqueous sodium hydroxide
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-7791cb12a34247d2a791e2f25ac79b9e
Source dataset
uspto-grants-2007_08
Patent number
US07262192B2

Reaction notes

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