Nitrogen → HCID 66928541, compound

HRID 2064923Notes

Reaction equation

N#N.C[O:4][C:5]([C:7]1[O:8][C:9]([CH2:12][N:13]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[N:14]2)=[CH:10][CH:11]=1)=O.CC(C[AlH]CC(C)C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1.C1(C)C=CC=CC=1>[N+:18]([C:15]1[CH:16]=[CH:17][N:13]([CH2:12][C:9]2[O:8][C:7]([CH2:5][OH:4])=[CH:11][CH:10]=2)[N:14]=1)([O-:20])=[O:19]

Participants

Conditions

Temperature: -78 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 5-(3-nitro-pyrazol-1-ylmethyl)-furan-2-carboxylic acid methyl ester (25.40 g, 61.31 mmol) in THF (154.0 mL) was treated dropwise, at −78° C. with DiBAL (165.0 mL of a 1.7M solution in toluene, 245.22 mmol). The reaction mixture was stirred at −78° C. for 1 h and then allowed to warm up to rt. Sat. aq. Rochelle's salt (600 mL) was added and the reaction mixture was stirred at rt for 2 h. The aq. layer was extracted with EA (2×500 mL) and the combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (40:60 hept-EA) gave the title compound. TLC: rf (40:60 hept-EA)=0.28. LC-MS-conditions 02: tR=0.75 min. 1H NMR (400 MHz, CDCl3) δ 2.05 (s, 1H), 4.60 (s, 2H), 5.36 (s, 2H), 6.31 (d, J=3.0 Hz, 1H), 6.46 (d, J=3.0 Hz, 1H), 6.91 (d, J=2.5 Hz, 1H), 7.51 (d, J=2.5 Hz, 1H).

Workup

temperatureto warm up to rt
stirringthe reaction mixture was stirred at rt for 2 h
extractionThe aq. layer was extracted with EA (2×500 mL)
dry with materialextracts were dried over MgSO4
filtrationfiltered
customthe solvents were removed under reduced pressure
customPurification of the residue by FC (40:60 hept-EA)

Sources & evidence

ORD record: ord-930b5aaf0ed2460fb517bc80fbb23a86
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288419B2

Reaction notes

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