Dimethylamine → Methyl 3-(dimethylamino)cyclobutanecarboxylate

HRID 626567Notes

Reaction equation

HRID 626567 reaction equation
O=[C:2]1[CH2:5][CH:4]([C:6]([O:8][CH3:9])=[O:7])[CH2:3]1.[CH3:10][NH:11][CH3:12].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>CCOC(C)=O>[CH3:10][N:11]([CH3:12])[CH:2]1[CH2:5][CH:4]([C:6]([O:8][CH3:9])=[O:7])[CH2:3]1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 13992367Methyl 3-oxocyclobutane-1-carboxylate

Product 1

HCID 90410277Methyl 3-(dimethylamino)cyclobutanecarboxylateYield 97.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 3-oxocyclobutanecarboxylate (0.5 g, 3.90 mmol) in EtOAc (10 mL) was treated with dimethylamine (1M in THF, 11.71 mL, 11.71 mmol), stirred at RT for 1 h, treated portion-wise with sodium triacetoxyborohydride (1.158 g, 5.46 mmol) and stirred at RT overnight. The mixture was treated with 1N NaOH, extracted with EtOAc (3×) and the combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness to afford methyl 3-(dimethylamino)cyclobutanecarboxylate (596 mg, 97%). 1H NMR (400 MHz, DMSO-d6): δ 3.57 (s, 3H), 3.33-3.26 (m, 1H), 2.75-2.74 (m, 1H), 2.19-2.18 (m, 2H), 1.97 (s, 6H), 1.88-1.85 (m, 2H).

Workup

  1. stirringstirred at RT overnight
  2. extractionextracted with EtOAc (3×)
  3. washthe combined organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-c29464bca4794877baff3766904124ae
Source dataset
uspto-grants-2016_04
Patent number
US09309224B2

Reaction notes

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