Methyl 4-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-3-carboxylate → [4-Nitro-1-(oxan-2-yl)-1H-pyrazol-3-yl]methanol

HRID 2064682Notes

Reaction equation

HRID 2064682 reaction equation
C[O:2][C:3]([C:5]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][N:7]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][O:14]2)[N:6]=1)=O.[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1.C(OCC)C>[N+:10]([C:9]1[C:5]([CH2:3][OH:2])=[N:6][N:7]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][O:14]2)[CH:8]=1)([O-:12])=[O:11]

Participants

5

Reactant 2

HCID 20784940Methyl 4-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-3-carboxylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 22477717[4-Nitro-1-(oxan-2-yl)-1H-pyrazol-3-yl]methanolYield 78.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred solution of 4-nitro-1-(tetrahydro-pyran-2-yl)-1H-pyrazole-3-carboxylic acid methyl ester [500 mg, Reference Example 54(a)] in tetrahydrofuran (20 ml) under nitrogen at −78° C. was treated dropwise with a solution of diisobutylaluminium hydride in tetrahydrofuran (8.82 ml, 1M). The reaction mixture was stirred at room temperature for 1.5 hours. The reaction mixture was taken up in diethyl ether (100 ml) and quenched with water (150 ml). The resulting suspension was filtered through celite and the organic layer was collected from the filtrate, then dried over magnesium sulfate and then evaporated to yield [4-nitro-1-(tetrahydro-pyran-2-yl)-1H-pyrazol-3-yl]-methanol (349 mg) as a peach oil. LC-MS (Method H): RT=2.08 minutes, 250.29 (M+H+ Na)+.

Workup

  1. customquenched with water (150 ml)
  2. filtrationThe resulting suspension was filtered through celite
  3. customthe organic layer was collected from the filtrate
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-d7d3fc8d737d43feb314e54476743498
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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