Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → (5R)-5-(hydroxymethyl)-4-oxaspiro[2.4]heptane
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]1Participants
4
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
- concentrationconcentrated in vacuo
- customThe residue was purified by a silica gel column chromatography (CH2Cl2)
Sources & evidence
- ORD record
- ord-a361cd92d57e40c9b310207db7b7d707
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08293897B2
Reaction notes
Loading…