Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → (5R)-5-(hydroxymethyl)-4-oxaspiro[2.4]heptane

HRID 1969381Notes

Reaction equation

HRID 1969381 reaction equation
O1CCCCC1[O:7][CH2:8][C@H:9]1[CH2:15][CH2:14][C:11]2([CH2:13][CH2:12]2)[O:10]1.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>CO>[OH:7][CH2:8][C@H:9]1[CH2:15][CH2:14][C:11]2([CH2:13][CH2:12]2)[O:10]1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 67296659(5R)-5-((tetrahydro-2H-pyran-2-yloxy)methyl)-4-oxaspiro[2.4]heptane

Product 1

HCID 67296758(5R)-5-(hydroxymethyl)-4-oxaspiro[2.4]heptaneYield 89.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of (5R)-5-((tetrahydro-2H-pyran-2-yloxy)methyl)-4-oxaspiro[2.4]heptane (101 mg, 0.48 mmol) in 5 mL of MeOH was added PPTS (12.1 mg, 0.048 mol, Aldrich) at room temperature. The reaction mixture was stirred at 40° C. overnight and then concentrated in vacuo. The residue was purified by a silica gel column chromatography (CH2Cl2) to give the title compound as colorless oil (55 mg, 89%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by a silica gel column chromatography (CH2Cl2)

Sources & evidence

ORD record
ord-787f81dee46d4995b0521261d366c0af
Source dataset
uspto-grants-2013_04
Patent number
US08426585B2

Reaction notes

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