tert-butyl N-(2-methyl-4-oxobutan-2-yl)carbamate → Tert-butyl {3-[2-(1-hydroxycyclohexyl)phenylamino]-1,1-dimethylpropyl}carbamate

HRID 1867335Notes

Reaction equation

HRID 1867335 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([OH:14])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[CH3:15][C:16]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:20])[CH2:17][CH:18]=O>CCCCCC.CCOC(C)=O>[OH:14][C:8]1([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH:1][CH2:18][CH2:17][C:16]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:20])[CH3:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 11788901tert-butyl N-(2-methyl-4-oxobutan-2-yl)carbamateHCID 135545281-(2-Aminophenyl)cyclohexan-1-ol

Product 1

HCID 86600982Tert-butyl {3-[2-(1-hydroxycyclohexyl)phenylamino]-1,1-dimethylpropyl}carbamate

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent2×

Procedure

The product is prepared analogously to intermediate product 1b starting from 1-(2-aminophenyl)cyclohexanol and tert-butyl (1,1-dimethyl-3-oxopropyl)carbamate. After column chromatography (silica gel, hexane/EtOAc 7:1) the product is obtained as a colorless oil. Yield: 2.65 g (66%); Rf=0.50 (silica gel, hexane/EtOAc 4:1).

Sources & evidence

ORD record
ord-1b832b0984ef41dd9a1e0b28b320d152
Source dataset
uspto-grants-2009_12
Patent number
US07632834B2

Reaction notes

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