Hydrochloric Acid → HCID 70553944, compound

HRID 1390484Notes

Reaction equation

HRID 1390484 reaction equation
Cl.C(NC(C(C1C=CC(O)=C(O)C=1)=O)C)(C)(C)C.C([Cl:25])(=O)C(C)(C)C.FC(F)(F)C(O)=O.Cl.Cl.[C:35]([NH:39][CH:40]([C:42]([C:44]1[CH:49]=[CH:48][C:47]([O:50][C:51](=[O:56])[C:52]([CH3:55])([CH3:54])[CH3:53])=[C:46]([O:57][C:58](=[O:63])[C:59]([CH3:62])([CH3:61])[CH3:60])[CH:45]=1)=[O:43])[CH3:41])([CH3:38])([CH3:37])[CH3:36]>[Pd]>[ClH:25].[C:58]([O:57][C:46]1[CH:45]=[C:44]([CH:49]=[CH:48][C:47]=1[O:50][C:51](=[O:56])[C:52]([CH3:55])([CH3:54])[CH3:53])[CH:42]([OH:43])[CH:40]([NH:39][C:35]([CH3:36])([CH3:37])[CH3:38])[CH3:41])(=[O:63])[C:59]([CH3:60])([CH3:61])[CH3:62]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 62493Pivaloyl chlorideHCID 20535228HCID 20535228, compoundHCID 20535451HCID 20535451, compound

Product 1

HCID 70553944HCID 70553944, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

3,4-Dihydroxyphenyl 1-(tert-butylamino)ethyl ketone hydrochloride (8 g.) was reacted with 18 ml. of pivalyl chloride in 35 ml. of trifluoroacetic acid, the resulting ester-amine salt was converted to the ester-amine, and the ester-amine was treated with hydrochloric acid to yield 10.5 g. of 3,4-bis(pivalyloxy)phenyl 1-(tert-butylamino)ethyl ketone hydrochloride, m.p. 200°-202° C. (uncorr.). This ketone was catalytically hydrogenated in the presence of palladium-on-charcoal catalyst to yield 3,4-bis(pivalyloxy)-alpha-[1-(tert-butylamino)ethyl]benzyl alcohol hydrochloride as a white crystalline solid which melted at 205°-207° C. (uncorr.).

Workup

  1. customto yield 10.5 g

Sources & evidence

ORD record
ord-627a2e140e9a49b590cae01e5317c545
Source dataset
uspto-grants-1979_02
Patent number
US04138581

Reaction notes

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