(S)-Ethyl 2-(2-(acetoxymethyl)-5-cyclohexenyl-7-methylquinolin-6-yl)-2-tert-butoxyacetate → (S)-Ethyl 2-tert-butoxy-2-(5-cyclohexenyl-2-(hydroxymethyl)-7-methylquinolin-6-yl)acetate

HRID 931780Notes

Reaction equation

HRID 931780 reaction equation
C([O:4][CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][C:10]([CH3:34])=[C:11]([C@H:23]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:12]=2[C:16]2[CH:21]=[CH:20][C:19](Cl)=[CH:18][CH:17]=2)[N:7]=1)(=O)C.C(OCC1C=CC2C(=CC(C)=C([C@H](OC(C)(C)C)C(OCC)=O)C=2C2CCCCC=2)N=1)(=O)C>>[C:30]([O:29][C@@H:23]([C:11]1[C:12]([C:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]=2)=[C:13]2[C:8](=[CH:9][C:10]=1[CH3:34])[N:7]=[C:6]([CH2:5][OH:4])[CH:15]=[CH:14]2)[C:24]([O:26][CH2:27][CH3:28])=[O:25])([CH3:31])([CH3:32])[CH3:33]

Participants

3

Reactant 2

HCID 68594582(S)-Ethyl 2-(2-(acetoxymethyl)-5-cyclohexenyl-7-methylquinolin-6-yl)-2-tert-butoxyacetateHCID 86691980(S)-ethyl 2-(2-(acetoxymethyl)-5-(4-chlorophenyl)-7-methylquinolin-6-yl)-2-tert-butoxyacetate

Product 1

HCID 68594629(S)-Ethyl 2-tert-butoxy-2-(5-cyclohexenyl-2-(hydroxymethyl)-7-methylquinolin-6-yl)acetate

Procedure

(S)-Ethyl 2-tert-butoxy-2-(5-cyclohexenyl-2-(hydroxymethyl)-7-methylquinolin-6-yl)acetate was prepared following the procedure used to prepare compound (S)-ethyl 2-tert-butoxy-2-(5-(4-chlorophenyl)-2-(hydroxymethyl)-7-methylquinolin-6-yl)acetate of Example 16, except that (S)-ethyl 2-(2-(acetoxymethyl)-5-cyclohexenyl-7-methylquinolin-6-yl)-2-tert-butoxyacetate was used instead of (S)-ethyl 2-(2-(acetoxymethyl)-5-(4-chlorophenyl)-7-methylquinolin-6-yl)-2-tert-butoxyacetate. LCMS-ESI+ (m/z): 412.3 (M+H)+.

Sources & evidence

ORD record
ord-6c44af042a9f4bdd97e39fd480efdb8c
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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