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

HRID 62448
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HRID 62448 반응식
[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]
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참가 물질

4

반응물 2

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

생성물 1

HCID 903041681-tosyl-4,5,6,7-tetrahydro-1H-indazol-4-ol수율 98.2%

시약·촉매·용매 1

HCID 21873804Tetrahydrofuran ethanol용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-79a1b44a121d45a4a7859a7efd3e18eb
출처 데이터셋
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09446130B2

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