Sodium cyanoborohydride → HCID 86632835, compound

HRID 2426772Notes

Reaction equation

HRID 2426772 reaction equation
C([BH3-])#N.[Na+].[Si:5]([O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:24]([CH3:25])=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:26])=[CH:15][C:14]=1[CH2:27][O:28][C:29]1[CH:37]=[CH:36][C:32]([CH:33]=[N:34][OH:35])=[CH:31][CH:30]=1)([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6].O1CCOCC1.Cl>CO.C1COCC1>[Si:5]([O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[C:20]([CH3:26])=[CH:21][CH:22]=[CH:23][C:24]=2[CH3:25])=[CH:15][C:14]=1[CH2:27][O:28][C:29]1[CH:37]=[CH:36][C:32]([CH2:33][NH:34][OH:35])=[CH:31][CH:30]=1)([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 204431481,4-Dioxane hydrochlorideHCID 86632836HCID 86632836, compound

Product 1

HCID 86632835HCID 86632835, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Hydroxylamine hydrochloride and a sodium acetate aqueous solution were added to an ethanol solution of 4-[(4′-chloro-2′-methylbiphenyl-3-yl)methoxy]benzaldehyde, followed by stirring at room temperature for 18 hours to obtain 4-[(4-{[tert-butyl(dimethyl)silyl]oxy}-2′,6′-dimethylbiphenyl-3-yl)methoxy]benzaldehyde oxime. Sodium cyanoborohydride was added to a methanol-THF mixed solution of the resulting 4-[(4-{[tert-butyl(dimethyl)silyl]oxy}-2′,6′-dimethylbiphenyl-3-yl)methoxy]benzaldehyde oxime, and then a 4 M hydrogen chloride dioxane solution was dropwise added thereto, followed by stirring at room temperature for 1 hour to obtain N-{4-[(4-{[tert-butyl(dimethyl)silyl]oxy}-2′,6′-dimethylbiphenyl-3-yl)methoxy]benzyl)hydroxylamine.

Sources & evidence

ORD record
ord-75b126d117f44cdfba6c9beb2705b162
Source dataset
uspto-grants-2011_06
Patent number
US07968552B2

Reaction notes

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