Methanol → Methyl 6-((tert-butoxycarbonyl)methyl)-2,2-dimethyl-1,3-dioxane-4-carboxylate

HRID 249548Notes

Reaction equation

HRID 249548 reaction equation
[OH:1][CH:2]([CH2:7][CH:8]([OH:17])[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:3]([O:5][CH3:6])=[O:4].CO[C:20](OC)([CH3:22])[CH3:21].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.CO>C(Cl)Cl>[CH3:6][O:5][C:3]([CH:2]1[CH2:7][CH:8]([CH2:9][C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])[O:17][C:20]([CH3:22])([CH3:21])[O:1]1)=[O:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 64952,2-DimethoxypropaneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 19761818HCID 19761818, compound

Product 1

HCID 19761812Methyl 6-((tert-butoxycarbonyl)methyl)-2,2-dimethyl-1,3-dioxane-4-carboxylateYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-methyl 6-tert.-butyl 2,4-dihydroxyadipate (4.98 g, 20.01 mmol) in methylene chloride (2 dimethoxypropane (9.6 ml, 78 mmol) and pyridinium p-toluenesulfonate (2.01 g, 8 mmol) were added and stirred under reflux conditions for one hour, followed by further stirring at 40° C. for 3 hours while azeotropically removing methanol with methylene chloride. After concentration under reduced pressure, the residue was dissolved in ethyl acetate and poured in water. Then, the mixture was extracted with ethyl acetate. The organic layers were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane:acetone=3:1) to give pure 2-methoxycarbonyl-4-tert.-butoxycarbonylmethyl-6,6-dimethyl-1,5-dioxane (4.89 g, 17.01 mmol). Yield, 85 %.

Workup

  1. concentrationAfter concentration under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. additionpoured in water
  4. extractionThen, the mixture was extracted with ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-af060e5b6faf427da41be637c23dbdb8
Source dataset
uspto-grants-1993_05
Patent number
US05214197

Reaction notes

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