Acetone → Methyl2-ethyl-2-[(propan-2-ylamino)methyl]butanoate

HRID 2234470Notes

Reaction equation

HRID 2234470 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]([CH2:9][NH2:10])([CH2:7][CH3:8])[CH2:5][CH3:6].[CH3:12][C:13]([CH3:15])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[CH3:1][O:2][C:3](=[O:11])[C:4]([CH2:5][CH3:6])([CH2:9][NH:10][CH:13]([CH3:15])[CH3:12])[CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 62596586Methyl 2-(aminomethyl)-2-ethylbutanoate2×

Product 1

HCID 86617586Methyl2-ethyl-2-[(propan-2-ylamino)methyl]butanoateYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl2-(aminomethyl)-2-ethyl-butanoate (Intermediate 201; 8 g, 50 mmol) and acetone (4.35 g, 75 mmol) were added to methanol (230 mL) and stirred for 10 minutes before the rapid addition of sodium triacetoxyborohydride (15.9 g, 75 mmol). The reaction was stirred overnight before being evaporated to dryness. The residue was quenched with saturated K2CO3(aq) (100 mL), extracted with DCM (3×150 mL), dried and solvent evaporated to yield a dark liquids. Purification was achieved via distillation (65 oC @ 0.18 mbar) to yield the title compound as clear oil (5.3 g, 53%)

Workup

  1. custombefore being evaporated to dryness
  2. customThe residue was quenched with saturated K2CO3(aq) (100 mL)
  3. extractionextracted with DCM (3×150 mL)
  4. customdried
  5. customsolvent evaporated
  6. customto yield a dark liquids
  7. customPurification
  8. distillationwas achieved via distillation (65 oC @ 0.18 mbar)

Sources & evidence

ORD record
ord-007c6d89587e4a7d88c5ef168e61b81e
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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