Piperidine → (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(piperidin-1-ylmethyl)quinolin-6-yl)ethyl pivalate

HRID 931759Notes

Reaction equation

HRID 931759 reaction equation
C(OC[C@H](C1C(Br)=[C:17]2[C:22](=CC=1C)[N:21]=[C:20](CN(C)C)[CH:19]=[CH:18]2)OC(C)(C)C)(=O)C(C)(C)C.[C:31]([O:35][C@@H:36]([C:45]1[C:46]([C:58]2[CH:63]=[CH:62][C:61]([Cl:64])=[CH:60][CH:59]=2)=[C:47]2[C:52](=[CH:53][C:54]=1[CH3:55])[N+:51]([O-])=[C:50]([CH3:57])[CH:49]=[CH:48]2)[CH2:37][O:38][C:39](=[O:44])[C:40]([CH3:43])([CH3:42])[CH3:41])([CH3:34])([CH3:33])[CH3:32].N1CCCCC1>>[C:39]([O:38][CH2:37][C@@H:36]([O:35][C:31]([CH3:34])([CH3:33])[CH3:32])[C:45]1[C:46]([C:58]2[CH:63]=[CH:62][C:61]([Cl:64])=[CH:60][CH:59]=2)=[C:47]2[C:52](=[CH:53][C:54]=1[CH3:55])[N:51]=[C:50]([CH2:57][N:21]1[CH2:22][CH2:17][CH2:18][CH2:19][CH2:20]1)[CH:49]=[CH:48]2)(=[O:44])[C:40]([CH3:43])([CH3:42])[CH3:41]

Participants

4

Reactant 3

HCID 8082PiperidineHCID 66631094(S)-6-(1-tert-Butoxy-2-(pivaloyloxy)ethyl)-5-(4-chlorophenyl)-2,7-dimethylquinoline 1-oxideHCID 66631121(S)-2-(5-bromo-2-((dimethylamino)methyl)-7-methylquinolin-6-yl)-2-tert-butoxyethyl pivalate

Product 1

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

Procedure

(S)-2-tert-Butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(piperidin-1-ylmethyl)quinolin-6-yl)ethyl pivalate was prepared following the procedure used to prepare compound (S)-2-(5-bromo-2-((dimethylamino)methyl)-7-methylquinolin-6-yl)-2-tert-butoxyethyl pivalate of Example 9, except that (S)-6-(1-tert-butoxy-2-(pivaloyloxy)ethyl)-5-(4-chlorophenyl)-2,7-dimethylquinoline 1-oxide was used instead of (S)-5-bromo-6-(1-tert-butoxy-2-(pivaloyloxy)ethyl)-2,7-dimethylquinoline 1-oxide, and piperidine was used instead of N,N-dimethylamine solution. LCMS-ESI+ (m/z): 551.3, 553.3 (M+H)+.

Sources & evidence

ORD record
ord-dda44bd1c9ba42d99aaa4610a1acb008
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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