p-Toluenesulfonic acid monohydrate → 1-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-3-nitro-1H-pyrazole

HRID 2381285Notes

Reaction equation

[N+:1]([C:4]1[CH:8]=[CH:7][N:6]([CH2:9][C@H:10]([OH:13])[CH2:11][OH:12])[N:5]=1)([O-:3])=[O:2].O.[C:15]1(C)[CH:20]=CC(S(O)(=O)=O)=C[CH:16]=1>COC(OC)(C)C.O1CCCC1>[CH3:16][C:15]1([CH3:20])[O:13][C@@H:10]([CH2:9][N:6]2[CH:7]=[CH:8][C:4]([N+:1]([O-:3])=[O:2])=[N:5]2)[CH2:11][O:12]1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of (S)-3-(3-nitro-pyrazol-1-yl)-propane-1,2-diol (1 g, 5.34 mmol) in 2,2-dimethoxypropane (8.5 mL, 0.63M) and tetrahydrofuran (10 mL, 0.53 M) was treated with para-toluenesulfonic acid monohydrate (0.11 g, 0.57 mmol). The reaction was stirred under nitrogen at 25° C. overnight. After this time, the reaction was concentrated in vacuo. Silica gel column chromatography (Aspire 40 g, 20-45% ethyl acetate/hexanes) afforded 1-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-3-nitro-1H-pyrazole (348.5 mg, 29%) as a viscous yellow/orange oil. The material was used without further purification.

Workup

concentrationAfter this time, the reaction was concentrated in vacuo

Sources & evidence

ORD record: ord-79854ee0ff2b491bb184140fb64207a7
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258134B2

Reaction notes

Loading…