HCID 67958890, compound → [2-(5-Formyl-3-phenoxymethyl-pyrazol-1-yl)-ethyl]-carbamic acid tert-butyl ester

HRID 1773793Notes

Reaction equation

[C:1]([O:5][C:6](=[O:25])[NH:7][CH2:8][CH2:9][N:10]1[C:14]([CH2:15][OH:16])=[CH:13][C:12]([CH2:17][O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:11]1)([CH3:4])([CH3:3])[CH3:2]>O1CCOCC1.[O-2].[O-2].[Mn+4]>[C:1]([O:5][C:6](=[O:25])[NH:7][CH2:8][CH2:9][N:10]1[C:14]([CH:15]=[O:16])=[CH:13][C:12]([CH2:17][O:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[N:11]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 100 °C

Procedure

Manganese dioxide (6.94 g, 79.9 mmol) was added portionwise to a stirred solution of [2-(5-hydroxymethyl-3-phenoxymethyl-pyrazol-1-yl)-ethyl]-carbamic acid tert-butyl ester (2.5 g, 5.33 mmol) in 1,4-dioxane (45 mL). The mixture was stirred at 100° C. for 16 hours and then filtered through a pad of diatomaceous earth. The solvents were evaporated in vacuo and the crude product was purified by flash column chromatography (silica; AcOEt in heptane 0/100 to 50/50). The desired fractions were collected and the solvents were evaporated in vacuo to yield [2-(5-formyl-3-phenoxymethyl-pyrazol-1-yl)-ethyl]-carbamic acid tert-butyl ester (0.81 g, 44% yield) as a yellow solid.

Workup

filtrationfiltered through a pad of diatomaceous earth
customThe solvents were evaporated in vacuo
customthe crude product was purified by flash column chromatography (silica; AcOEt in heptane 0/100 to 50/50)
customThe desired fractions were collected
customthe solvents were evaporated in vacuo

Sources & evidence

ORD record: ord-0fb1099b606a46358e166d5fcf123c81
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255103B2

Reaction notes

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