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 2182423Notes

Reaction equation

HRID 2182423 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-269b51dd84d54e4cb40d91a6dde8812a
Source dataset
uspto-grants-2005_05
Patent number
US06897208B2

Reaction notes

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