4-(Hydroxymethyl)benzeneboronic acid → tert-Butyl 3-(1-(4-(2,3-dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)benzylcarbamate

HRID 2175247Notes

Reaction equation

HRID 2175247 reaction equation
[CH3:1][C:2]1[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([N:10]1[C:19]2[C:14](=[C:15](C3C=CC(CO)=CC=3)[CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1)=[O:9].OCC1C=CC(B(O)O)=CC=1.CC1(C)C(C)(C)OB([C:52]2[CH:53]=[C:54]([CH:64]=[CH:65][CH:66]=2)[CH2:55][NH:56][C:57](=[O:63])[O:58][C:59]([CH3:62])([CH3:61])[CH3:60])O1>>[CH3:1][C:2]1[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][C:8]([N:10]1[C:19]2[C:14](=[C:15]([C:52]3[CH:53]=[C:54]([CH:64]=[CH:65][CH:66]=3)[CH2:55][NH:56][C:57](=[O:63])[O:58][C:59]([CH3:60])([CH3:61])[CH3:62])[CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1)=[O:9]

Participants

4

Reactant 3

HCID 27347064-(Hydroxymethyl)benzeneboronic acidHCID 2760591tert-Butyl {[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}carbamateHCID 709818684-(2,3-Dimethylphenoxy)-1-(5-(4-(hydroxymethyl)phenyl)-3,4-dihydroquinolin-1(2H)-yl)butan-1-one

Product 1

HCID 70982891tert-Butyl 3-(1-(4-(2,3-dimethylphenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)benzylcarbamate

Procedure

The title compound was prepared using a procedure analogous to 4-(2,3-dimethylphenoxy)-1-(5-(4-(hydroxymethyl)phenyl)-3,4-dihydroquinolin-1(2H)-yl)butan-1-one except that 4-(hydroxymethyl)phenylboronic acid was replaced with tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylcarbamate. LCMS, [M+Na]+=551.4.

Sources & evidence

ORD record
ord-e35e47ff1de64dfcaa9179d7f2c6418b
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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