Triethylamine → HCID 58399448, compound

HRID 1802529Notes

Reaction equation

HRID 1802529 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1([CH2:20][OH:21])[CH2:19][CH2:18][C:13]2([O:17][CH2:16][CH2:15][O:14]2)[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C>CS(C)=O>[CH2:1]([O:8][CH2:9][C:10]1([CH:20]=[O:21])[CH2:19][CH2:18][C:13]2([O:14][CH2:15][CH2:16][O:17]2)[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 58399365(8-(Benzyloxymethyl)-1,4-dioxaspiro[4.5]decan-8-yl)methanol

Product 1

HCID 58399448HCID 58399448, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of (8-(benzyloxymethyl)-1,4-dioxaspiro[4.5]decan-8-yl)methanol (Reference Example 85) (183 mg, 0.625 mmol) in dimethyl sulfoxide (2.1 mL), 50% sulfur trioxide-pyridine complex (596 mg, 1.87 mmol) and triethylamine (0.522 mL, 3.75 mmol) were added, and the obtained solution was stirred at room temperature for 20 minutes. The reaction was quenched by adding water to the reaction solution, and the resulting solution was extracted with ethyl acetate. The organic layer was washed sequentially with 20% aqueous citric acid solution, saturated sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, n-hexane/ethyl acetate) to obtain the captioned compound (172 mg, 0.592 mmol, 95%) as a colorless oily compound.

Workup

  1. customThe reaction was quenched
  2. additionby adding water to the reaction solution
  3. extractionthe resulting solution was extracted with ethyl acetate
  4. washThe organic layer was washed sequentially with 20% aqueous citric acid solution, saturated sodium bicarbonate solution and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (silica gel, n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-71fb919342294389b81139d2ce8ecf6d
Source dataset
uspto-grants-2013_01
Patent number
US08349874B2

Reaction notes

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