Cyclohexanecarbonyl chloride → 3,4-Bis(1,3-dimethylcyclobutanecarbonyloxy)-alpha-(tert-butylaminomethyl)benzyl alcohol

HRID 1156663Notes

Reaction equation

CC1(C(Cl)=O)CC(C)C1.C1(C(Cl)=O)CCCCC1.[C:19]([NH:23][CH2:24][C:25]([C:27]1[CH:32]=[CH:31][C:30]([O:33][C:34]([CH:36]([CH3:41])[CH2:37][CH:38]([CH3:40])[CH3:39])=[O:35])=[C:29]([O:42][C:43]([CH:45]([CH3:50])[CH2:46][CH:47]([CH3:49])[CH3:48])=[O:44])[CH:28]=1)=[O:26])([CH3:22])([CH3:21])[CH3:20]>>[CH3:50][C:45]1([C:43]([O:42][C:29]2[CH:28]=[C:27]([CH:32]=[CH:31][C:30]=2[O:33][C:34]([C:36]2([CH3:41])[CH2:40][CH:38]([CH3:39])[CH2:37]2)=[O:35])[CH:25]([OH:26])[CH2:24][NH:23][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:44])[CH2:48][CH:47]([CH3:49])[CH2:46]1

Participants

Reactant 3

HCID 75938Cyclohexanecarbonyl chloride

HCID 205353791,3-Dimethylcyclobutanecarbonyl chloride

HCID 205354353,4-Bis(1,3-dimethylbutanecarbonyloxy)phenyl tert-butylaminomethyl ketone

Product 1

HCID 536401893,4-Bis(1,3-dimethylcyclobutanecarbonyloxy)-alpha-(tert-butylaminomethyl)benzyl alcohol

Procedure

When 1,3-dimethylcyclobutanecarbonyl chloride is substituted for the cyclohexanecarbonyl chloride in the procedure described in Example 15A above, the acylation product obtained is 3,4-bis(1,3-dimethylbutanecarbonyloxy)phenyl tert-butylaminomethyl ketone; and when this product is catalytically hydrogenated using the procedure described in Example 15B above, there is obtained 3,4-bis(1,3-dimethylcyclobutanecarbonyloxy)-alpha-(tert-butylaminomethyl)benzyl alcohol.

Workup

customobtained

Sources & evidence

ORD record: ord-f979fb9d3e3b45159d0b06fa8df73be7
Source dataset: uspto-grants-1982_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04336400

Reaction notes

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