Potassium Sodium Tartrate → (6-(Benzyloxy)-1-(tetrahydro-2H-pyran-2-yl)indazol-3-yl)methanol

HRID 1873956Notes

Reaction equation

HRID 1873956 reaction equation
C([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:12][CH:13]=2)[N:8]([CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)[N:7]=1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+].C(=O)([O-])O.[Na+]>C1COCC1.C1COCC1.O>[CH2:16]([O:15][C:11]1[CH:10]=[C:9]2[C:14]([C:6]([CH2:4][OH:3])=[N:7][N:8]2[CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)=[CH:13][CH:12]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 9357Potassium Sodium TartrateHCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 59370773Ethyl 6-benzyloxy-1-(tetrahydro-2H-pyran-2-yl)indazole-3-carboxylate

Product 1

HCID 59370714(6-(Benzyloxy)-1-(tetrahydro-2H-pyran-2-yl)indazol-3-yl)methanolYield 95.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

Ethyl6-benzyloxy-1-(tetrahydro-2H-pyran-2-yl)-indazole-3-carboxylate (182 mg) which can be prepared according to the method described in Reference example 21, etc. was dissolved in dehydrated THF (4.78 mL; manufactured by Kanto Chemical Co., Inc.). After the replacement with nitrogen, LiAlH4 (54 mg) was added at 0° C., and the mixture was stirred for 1 hour while warming to room temperature. After cooling to 0° C., THF/water=1/1(5 mL), rochelle salt (manufactured by Kanto Chemical Co., Inc.), and saturated aqueous solution of sodium hydrogen carbonate were added, and extraction was carried out twice with ethyl acetate. The organic layer was washed twice with water and once with brine and dried over anhydrous sodium sulfate. After the solvent was evaporated under reduced pressure, hexane was added to the residue and the solvent was evaporated under reduced pressure to give the title compound (155 mg).

Workup

  1. temperatureAfter cooling to 0° C.
  2. extractionextraction
  3. washThe organic layer was washed twice with water and once with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter the solvent was evaporated under reduced pressure, hexane
  6. additionwas added to the residue
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ec83bf7d67c346829a1e12a215131f79
Source dataset
uspto-grants-2012_11
Patent number
US08304443B2

Reaction notes

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