HCID 12295044, compound → Ammonium Hydroxide

HRID 1156656Notes

Reaction equation

HRID 1156656 reaction equation
[ClH:1].[C:2]([NH:6][CH2:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17](=[O:24])[C:18]([CH3:23])([CH3:22])[CH2:19][CH2:20][CH3:21])=[C:12]([O:25][C:26](=[O:33])[C:27]([CH3:32])([CH3:31])[CH2:28][CH2:29][CH3:30])[CH:11]=1)=[O:9])([CH3:5])([CH3:4])[CH3:3]>[Pd].C(O)C>[ClH:1].[CH3:32][C:27]([CH3:31])([CH2:28][CH2:29][CH3:30])[C:26]([O:25][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][C:13]=1[O:16][C:17](=[O:24])[C:18]([CH3:23])([CH3:22])[CH2:19][CH2:20][CH3:21])[CH:8]([OH:9])[CH2:7][NH:6][C:2]([CH3:3])([CH3:4])[CH3:5])=[O:33].[OH-:9].[NH4+:6]

Participants

5

Reactant 1

HCID 12295044HCID 12295044, compound

Product 2

HCID 14923Ammonium HydroxideYield 10%HCID 70554072HCID 70554072, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

By catalytic hydrogenation of 15 g. of 3,4-bis(2,2-dimethylpentanoyloxy)phenyl tert-butylaminomethyl ketone hydrochloride in 200 ml. of 95 percent ethyl alcohol in the presence of 2 g. of 10 percent palladium-on-charcoal catalyst there was obtained 3,4-bis(2,2-dimethylpentanoyloxy)-alpha-(tert-butylaminomethyl)benzyl alcohol hydrochloride which by treatment with an excess of 10 percent ammonium hydroxide was converted to the free base (11 g.). This base was converted to its methanesulfonic acid salt (10 g.), a white crystalline powder which melted at 107°-109° C. (uncorr.). The methanesulfonate was soluble in water at 25° C. to the extent of at least 5 percent.

Sources & evidence

ORD record
ord-caefd8e6bdc3424195a264b856cb3d4c
Source dataset
uspto-grants-1982_06
Patent number
US04336400

Reaction notes

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