2-Methylbenzenesulfonic acid → HCID 58951512, compound

HRID 2421221Notes

Reaction equation

HRID 2421221 reaction equation
[CH3:1][C:2]([O:11][CH2:12][C@@H:13]1[CH2:18][CH2:17][CH2:16][C@H:15]([O:19]C2CCCCO2)[CH2:14]1)([CH3:10])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].O.C1(C)C(S(O)(=O)=O)=CC=CC=1.C1(C)C(S(O)(=O)=O)=CC=CC=1.C(=O)(O)[O-].[Na+]>C(O)(C)C>[OH:19][C@H:15]1[CH2:16][CH2:17][CH2:18][C@@H:13]([CH2:12][O:11][C:2]([CH3:10])([CH3:1])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[CH2:14]1

Participants

6

Reactant 4

HCID 69252-Methylbenzenesulfonic acidHCID 516892Sodium BicarbonateHCID 124969952-Methylbenzenesulfonic acid hydrateHCID 58951517tert-butyl 2-methyl-2-[(1R,3S)-3-(tetrahydropyran-2-yloxy)cyclohexylmethoxy]-propionate

Product 1

HCID 58951512HCID 58951512, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

29 g of tert-butyl 2-methyl-2-[(1R,3S)-3-(tetrahydropyran-2-yloxy)cyclohexylmethoxy]-propionate are dissolved in 150 ml of isopropanol, and 2.3 g of toluenesulfonic acid monohydrate are added. After the toluenesulfonic acid has completely dissolved, the solution is left to stand for 4 days and then mixed with saturated sodium bicarbonate solution and partly concentrated. The residue is taken up MTBE/water, the phases are separated, the aqueous phase is extracted with MTBE, and the combined organic phases are dried over magnesium sulfate and concentrated. The residue is chromatographed on silica gel with heptane/ethyl acetate 3:1, resulting in 13.8 g of tert-butyl 2-((1R,3S)-3-hydroxycyclohexylmethoxy)-2-methylpropionate as yellow oil.

Workup

  1. waitthe solution is left
  2. concentrationpartly concentrated
  3. customthe phases are separated
  4. extractionthe aqueous phase is extracted with MTBE
  5. dry with materialthe combined organic phases are dried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue is chromatographed on silica gel with heptane/ethyl acetate 3:1
  8. customresulting in 13.8 g of tert-butyl 2-((1R,3S)-3-hydroxycyclohexylmethoxy)-2-methylpropionate as yellow oil

Sources & evidence

ORD record
ord-ed15e640e43d4c049c388629e4187cd7
Source dataset
uspto-grants-2011_06
Patent number
US07956077B2

Reaction notes

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