p-Toluenesulfonic acid → 1-(3-Nitro-pyrazol-1-ylmethyl)-cyclopropanol

HRID 546122Notes

Reaction equation

[N+:1]([C:4]1[CH:8]=[CH:7][N:6]([CH2:9][C:10]2([O:13]C3CCCCO3)[CH2:12][CH2:11]2)[N:5]=1)([O-:3])=[O:2].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[N+:1]([C:4]1[CH:8]=[CH:7][N:6]([CH2:9][C:10]2([OH:13])[CH2:12][CH2:11]2)[N:5]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 25 °C

Procedure

The 3-nitro-1-[1-(tetrahydro-pyran-2-yloxy)-cyclopropylmethyl]-1H-pyrazole (326 mg, 1.22 mmol) was dissolved in ethanol (7 mL) and p-toluene sulfonic acid (50 mg, 0.29 mmol) was added. After stirring at 25° C. for 1.5 h, the solution was concentrated in vacuo to give an oil. Purification by flash column chromatography (Merck silica gel 60, 40-63 μm; 50% ethyl acetate/hexanes) afforded 1-(3-nitro-pyrazol-1-ylmethyl)-cyclopropanol (158 mg, 71%) as an oil: H1-NMR (400 MHz, CDCl3) δ 0.81-0.86 (2H, m), 0.97-1.02 (2H, m), 2.78 (1H, bs), 4.31 (2H, s), 6.92 (1H, d, J=2.4 Hz), 7.61 (1H, d, J=2.4 Hz).

Workup

concentrationthe solution was concentrated in vacuo
customto give an oil
customPurification by flash column chromatography (Merck silica gel 60, 40-63 μm; 50% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-1b6bf4c3eb1040c89970d03f82c2549b
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935699B2

Reaction notes

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