Methanol → HCID 89389389, compound

HRID 62442Notes

Reaction equation

HRID 62442 reaction equation
[CH3:1][N:2]1[C:10]2[CH2:9][CH2:8][CH:7]=[C:6]([C:11]([O-:13])=[O:12])[C:5]=2[CH:4]=[N:3]1.[BH4-].[Na+].[CH3:16]O>Cl[Ni]Cl>[CH3:1][N:2]1[C:10]2[CH2:9][CH2:8][CH2:7][CH:6]([C:11]([O:13][CH3:16])=[O:12])[C:5]=2[CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 131737190HCID 131737190, compound

Product 1

HCID 89389389HCID 89389389, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 24385Nickel DichlorideCatalyst

Procedure

To a solution of 1-methyl-6,7-dihydro-1H-indazole-4-carboxylate (7.5 g, 38.7 mmol) and NiCl2 (4.9 g, 38.7 mmol) in MeOH (250 mL) was added NaBH4 (14 g, 387 mmol) in portions at 0° C. The resulting mixture was stirred at room temperature for further 1 hour. The solvent was removed and the residue was purified by column chromatography on silica gel (PE/THF=5/1 v/v %) to afford methyl 1-methyl-4,5,6,7-tetrahydro-1H-indazole-4-carboxylate (7 g, 94%).

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by column chromatography on silica gel (PE/THF=5/1 v/v %)

Sources & evidence

ORD record
ord-9b42b5b823984e21a5a413f1fe269360
Source dataset
uspto-grants-2016_09
Patent number
US09446130B2

Reaction notes

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