(S)-5-bromo-6-(1-tert-butoxy-2-ethoxy-2-oxoethyl)-2,7-dimethylquinoline 1-oxide → (S)-ethyl 2-tert-butoxy-2-(5-cyclohexenyl-2-((dimethylamino) methyl)-7-methylquinolin-6-yl)acetate

HRID 931781Notes

Reaction equation

HRID 931781 reaction equation
BrC1C([C@H](OC(C)(C)C)C(OCC)=O)=C(C)C=[C:8]2C=1C=C[C:6](C)=[N+:7]2[O-].[C:26]([O:30][C@@H:31]([C:37]1[C:38]([C:50]2[CH2:55][CH2:54][CH2:53][CH2:52][CH:51]=2)=[C:39]2[C:44](=[CH:45][C:46]=1[CH3:47])[N:43]=[C:42]([CH2:48]O)[CH:41]=[CH:40]2)[C:32]([O:34][CH2:35][CH3:36])=[O:33])([CH3:29])([CH3:28])[CH3:27]>>[C:26]([O:30][C@@H:31]([C:37]1[C:38]([C:50]2[CH2:55][CH2:54][CH2:53][CH2:52][CH:51]=2)=[C:39]2[C:44](=[CH:45][C:46]=1[CH3:47])[N:43]=[C:42]([CH2:48][N:7]([CH3:8])[CH3:6])[CH:41]=[CH:40]2)[C:32]([O:34][CH2:35][CH3:36])=[O:33])([CH3:29])([CH3:27])[CH3:28]

Participants

3

Reactant 2

HCID 66631477(S)-5-bromo-6-(1-tert-butoxy-2-ethoxy-2-oxoethyl)-2,7-dimethylquinoline 1-oxideHCID 68594629(S)-Ethyl 2-tert-butoxy-2-(5-cyclohexenyl-2-(hydroxymethyl)-7-methylquinolin-6-yl)acetate

Product 1

HCID 68586390(S)-ethyl 2-tert-butoxy-2-(5-cyclohexenyl-2-((dimethylamino) methyl)-7-methylquinolin-6-yl)acetate

Procedure

(S)-Ethyl 2-tert-Butoxy-2-(5-cyclohexenyl-2-((dimethylamino)methyl)-7-methylquinolin-6-yl)acetate was prepared following the procedure used to prepare compound (S)-ethyl 2-tert-butoxy-2-((R)-5-(2,3-dihydropyrano[4,3,2-de]quinolin-7-yl)-2-((dimethylamino)methyl)-7-methylquinolin-6-yl)acetate of Example 20 except that (S)-ethyl 2-tert-butoxy-2-(5-cyclohexenyl-2-(hydroxymethyl)-7-methylquinolin-6-yl)acetate was used instead of (S)-ethyl 2-tert-butoxy-2-((R)-5-(2,3-dihydropyrano[4,3,2-de]quinolin-7-yl)-2-(hydroxymethyl)-7-methylquinolin-6-yl)acetate. LCMS-ESI+ (m/z): 439.4 (M+H)+.

Sources & evidence

ORD record
ord-b496324279664ee4b8f43b4ad1cd3b1d
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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