Water → 4-Amino-4-[1-(4-chlorophenyl)cyclobutyl]-2-methylbutan-2-ol maleate

HRID 728273

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12](=[N:18]O)[CH2:13][C:14]([OH:17])([CH3:16])[CH3:15])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[BH4-].[Na+].O.[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]\[C:26]([OH:28])=[O:27]>CO.CCOCC.O[Mo](O)(=O)=O>[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]\[C:26]([OH:28])=[O:27].[NH2:18][CH:12]([C:8]1([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:9][CH2:10][CH2:11]1)[CH2:13][C:14]([CH3:16])([OH:17])[CH3:15]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 1-[1-(4-chlorophenyl)cyclobutyl]-3-hydroxy-3-methylbutan-1-one oxime (2 g) in methanol (70 ml) was cooled to -10° C. and molybdic acid (1.67 g) added with stirring. Sodium borohydride (2.7 g) was added portionwise. The temperature of the reaction mixture was maintained at 0° C. for 21/2 hours and then water (200 ml) was added. The reaction mixture was extracted with ether, the extract filtered, and the filtrate washed with water and dried. Removal of the solvents yielded an oil which was dissolved in ether. A solution of maleic acid in ether was added and a gum was formed which solidified to give 4-amino-4-[1-(4-chlorophenyl)cyclobutyl]-2-methylbutan-2-ol maleate (m.p. 139°-144° C. (dec)).

Workup

extractionThe reaction mixture was extracted with ether
filtrationthe extract filtered
washthe filtrate washed with water
customdried
customRemoval of the solvents
customyielded an oil which
customa gum was formed which

Sources & evidence

ORD record: ord-f60cd1d7155c459eab08064226917a22
Source dataset: uspto-grants-1991_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05047432

Linked notes

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