(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2-((dimethylamino)methyl)-7-methylquinolin-6-yl)ethanol → (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(piperidin-1-ylmethyl)quinolin-6-yl)ethanol

HRID 931760Notes

Reaction equation

HRID 931760 reaction equation
C(O[C@@H](C1C(C2C=CC(Cl)=CC=2)=C2C(=CC=1C)N=C(CN(C)C)C=C2)CO)(C)(C)C.C([O:37][CH2:38][C@@H:39]([O:65][C:66]([CH3:69])([CH3:68])[CH3:67])[C:40]1[C:41]([C:58]2[CH:63]=[CH:62][C:61]([Cl:64])=[CH:60][CH:59]=2)=[C:42]2[C:47](=[CH:48][C:49]=1[CH3:50])[N:46]=[C:45]([CH2:51][N:52]1[CH2:57][CH2:56][CH2:55][CH2:54][CH2:53]1)[CH:44]=[CH:43]2)(=O)C(C)(C)C>>[C:66]([O:65][C@@H:39]([C:40]1[C:41]([C:58]2[CH:59]=[CH:60][C:61]([Cl:64])=[CH:62][CH:63]=2)=[C:42]2[C:47](=[CH:48][C:49]=1[CH3:50])[N:46]=[C:45]([CH2:51][N:52]1[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57]1)[CH:44]=[CH:43]2)[CH2:38][OH:37])([CH3:69])([CH3:67])[CH3:68]

Participants

3

Reactant 2

HCID 66631647(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2-((dimethylamino)methyl)-7-methylquinolin-6-yl)ethanolHCID 66631687(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(piperidin-1-ylmethyl)quinolin-6-yl)ethyl pivalate

Product 1

HCID 66630435(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(piperidin-1-ylmethyl)quinolin-6-yl)ethanol

Procedure

(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(piperidin-1-ylmethyl)quinolin-6-yl)ethanol was prepared following the procedure used to prepare compound (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2-((dimethylamino)methyl)-7-methylquinolin-6-yl)ethanol of Example 9, except that (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(piperidin-1-ylmethyl)quinolin-6-yl)ethyl pivalate was used instead of (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2-((dimethylamino)methyl)-7-methylquinolin-6-yl)ethyl pivalate. LCMS-ESI+ (m/z): 467.4, 469.3 (M+H)+.

Sources & evidence

ORD record
ord-a49687ece15f487890b38921ac821726
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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