Triethylamine → 1-(N-t-butoxycarbonyl-N-methylamino)-2-oxo-5-methylhexane

HRID 847550Notes

Reaction equation

HRID 847550 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:10][CH:11]([OH:17])[CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C>CS(C)=O>[C:1]([O:5][C:6]([N:8]([CH2:10][C:11](=[O:17])[CH2:12][CH2:13][CH:14]([CH3:15])[CH3:16])[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 19753986N-t-butoxycarbonyl-N-methylamino-2-hydroxy-5-methylhexane

Product 1

HCID 197539251-(N-t-butoxycarbonyl-N-methylamino)-2-oxo-5-methylhexaneYield 88.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 1-(N-t-butoxycarbonyl-N-methylamino-2-hydroxy-5-methylhexane (2.45 g) and triethylamine (3.03 g) in dimethyl sulfoxide (20 ml) was added sulfur trioxide pyridine complex (4.77 g) under ice-bath cooling. After the mixture was stirred at ambient temperature overnight, the reaction mixture was poured into ice-water (100 ml). The mixture was extracted with diethyl ether (100 ml×2). The extract was washed with water, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (20% ethyl acetate in n-hexane as eluent) to give 1-(N-t-butoxycarbonyl-N-methylamino)-2-oxo-5-methylhexane (2.15 g).

Workup

  1. temperaturecooling
  2. extractionThe mixture was extracted with diethyl ether (100 ml×2)
  3. washThe extract was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified with silica gel column chromatography (20% ethyl acetate in n-hexane as eluent)

Sources & evidence

ORD record
ord-3a53f2e7437740898bcacfe1402b0681
Source dataset
uspto-grants-1992_08
Patent number
US05142048

Reaction notes

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