6-Benzyloxy-1-[(S)-2-(tert-butyldimethyl-silanyloxy)-propyl]-1H-indazole → 1-[(S)-2-(tert-Butyldimethyl-silanyloxy)-propyl]-1H-indazol-6-ol

HRID 1815960

Reaction equation

HRID 1815960 reaction equation
C([O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[N:14][N:15]2[CH2:18][C@@H:19]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH3:20])=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[C:25]([Si:22]([CH3:24])([CH3:23])[O:21][C@@H:19]([CH3:20])[CH2:18][N:15]1[C:16]2[C:12](=[CH:11][CH:10]=[C:9]([OH:8])[CH:17]=2)[CH:13]=[N:14]1)([CH3:27])([CH3:28])[CH3:26]

Participants

4

Reactant 1

HCID 695717436-Benzyloxy-1-[(S)-2-(tert-butyldimethyl-silanyloxy)-propyl]-1H-indazole

Product 1

HCID 1364116801-[(S)-2-(tert-Butyldimethyl-silanyloxy)-propyl]-1H-indazol-6-olYield 90.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of the product from Step A (5.44 g, 13.7 mmol) and palladium-on-carbon (10%, 0.50 g) in methanol (200 mL) was stirred under an atmosphere of hydrogen for 18 h, filtered and evaporated to give an off-white solid (3.80 g, 90%): mp 171-172° C.

Workup

  1. filtrationfiltered
  2. customevaporated

Sources & evidence

ORD record
ord-b83f797b975d4af7947fd744d5a61714
Source dataset
uspto-grants-2005_04
Patent number
US06881749B2

Linked notes

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