Sodium borohydride → 1-tosyl-4,5,6,7-tetrahydro-1H-indazol-4-ol

HRID 62448

Reaktionsgleichung

Reaktionsgleichung von HRID 62448
[S:1]([N:11]1[C:19]2[CH2:18][CH2:17][CH2:16][C:15](=[O:20])[C:14]=2[CH:13]=[N:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[BH4-].[Na+]>CCO.C1COCC1>[S:1]([N:11]1[C:19]2[CH2:18][CH2:17][CH2:16][CH:15]([OH:20])[C:14]=2[CH:13]=[N:12]1)([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=1)(=[O:3])=[O:2]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 674585881-tosyl-6,7-dihydro-1H-indazol-4(5H)-one

Produkt 1

HCID 903041681-tosyl-4,5,6,7-tetrahydro-1H-indazol-4-olAusbeute 98,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21873804Tetrahydrofuran ethanolLösungsmittel

Versuchsvorschrift

To a solution of 1-tosyl-6,7-dihydro-1H-indazol-4(5H)-one (5 g, 17.22 mmol) in EtOH/THF (30 mL/30 mL)) was added NaBH4 (1.3 g, 34.44 mmol) under ice-bath. The mixture was stirred for 1 h at this temperature and quenched with aqueous NH4Cl solution. Removed the solvent under reduced pressure and extracted with DCM and the combined organic layer was washed with water, brine and dried over anhydrous Na2SO4. The organic layer was concentrated in vacuo and the residue 1-tosyl-4,5,6,7-tetrahydro-1H-indazol-4-ol (4.94 g, yield 98.2%) was used directly to next step. MS-ESI (m/z): 293 (M+1)+ (Acq Method: 10-80AB_2 min; Rt: 1.01 min)

Aufarbeitung

  1. customquenched with aqueous NH4Cl solution
  2. customRemoved the solvent under reduced pressure
  3. extractionextracted with DCM
  4. washthe combined organic layer was washed with water, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationThe organic layer was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-79a1b44a121d45a4a7859a7efd3e18eb
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09446130B2

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