Methylamine → HCID 66935921, compound

HRID 1028225Notes

Reaction equation

HRID 1028225 reaction equation
O1CCCC1.[CH3:6][O:7][C:8](=[O:17])[CH2:9][CH:10]1[CH2:15][CH2:14][C:13](=O)[CH2:12][CH2:11]1.[CH3:18][NH2:19].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(=O)(O)[O-].[Na+].C(O)(=O)C>[CH3:6][O:7][C:8](=[O:17])[CH2:9][CH:10]1[CH2:15][CH2:14][CH:13]([NH:19][CH3:18])[CH2:12][CH2:11]1

Participants

7

Reactant 4

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 5049666Sodium triacetoxyborohydrideHCID 21249113Methyl 2-(4-oxocyclohexyl)acetate

Product 1

HCID 66935921HCID 66935921, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a tetrahydrofuran (60 mL) solution of (4-oxo-cyclohexyl)-acetic acid methyl ester (2.14 g) obtained in Example (1c), methylamine (2.0 M tetrahydrofuran solution, 12.5 mL), acetic acid (0.72 mL), and sodium triacetoxyborohydride (2.67 g) were added at room temperature. After 4 hours, the reaction mixture was diluted with saturated sodium bicarbonate (100 mL). The organic solvent was removed under reduced pressure. The aqueous mixture was subjected to extraction with dichloromethane (×3). The dichloromethane layer was dried over sodium sulfate and then concentrated. The residue was purified by column chromatography (NH silica gel, dichloromethane/methanol) to obtain the title compound (822 mg, 35%) as a brown oil.

Workup

  1. customThe organic solvent was removed under reduced pressure
  2. extractionThe aqueous mixture was subjected to extraction with dichloromethane (×3)
  3. dry with materialThe dichloromethane layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (NH silica gel, dichloromethane/methanol)

Sources & evidence

ORD record
ord-acdd79ccdd2f458490fb4aedc8ff0646
Source dataset
uspto-grants-2014_05
Patent number
US08735425B2

Reaction notes

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