Sulfuric Acid → [cyclopentyl-[(2S,4R)-4,5-diacetoxytetrahydrofuran-2-yl]methyl] benzoate

HRID 60705Notes

Reaction equation

HRID 60705 reaction equation
[C:1]([O:9][CH:10]([C@H:16]1[O:25][C@@H:19]2[O:20][C:21](C)([CH3:23])[O:22][C@@H:18]2[CH2:17]1)[CH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26](OC(=O)C)(=[O:28])[CH3:27].[OH:33]S(O)(=O)=O.C([O-])(O)=O.[Na+]>CCOC(C)=O.C(O)(=O)C>[C:1]([O:9][CH:10]([CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15]1)[C@@H:16]1[CH2:17][C@@H:18]([O:22][C:26](=[O:28])[CH3:27])[CH:19]([O:20][C:21](=[O:33])[CH3:23])[O:25]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 121396345[[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-cyclopentyl-methyl] benzoate2×

Product 1

HCID 121396365[cyclopentyl-[(2S,4R)-4,5-diacetoxytetrahydrofuran-2-yl]methyl] benzoate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of [[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-cyclopentyl-methyl] benzoate (compound 11b, 800 mg, 2.3 mmol) in the mixture of acetic acid (2 mL) and acetic acid anhydride (2 mL) was added H2SO4 (0.2 mmol). After being stirred at room temperature for 24 hours, the solution was diluted by EtOAc (40 mL) and adjusted to pH 5.0 by addition of saturated NaHCO3 solution. The organic layer was separated, washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 1:3 EtOAc in petroleum ether) to afford 480 mg of [cyclopentyl-[(2S,4R)-4,5-diacetoxytetrahydrofuran-2-yl]methyl] benzoate (compound 11c).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (eluting with 1:3 EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-b77a4100120941e3904a7bafbaba88ca
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Reaction notes

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