Sodium Hydroxide → (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-morpholinoquinolin-6-yl)ethanol

HRID 931792Notes

Reaction equation

C([O:7][CH2:8][C@@H:9]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])[C:10]1[C:11]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]=[C:15]([N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1)[CH:14]=[CH:13]2)(=O)C(C)(C)C.[OH-].[Na+]>C1COCC1.CO.O>[C:35]([O:34][C@@H:9]([C:10]1[C:11]([C:27]2[CH:28]=[CH:29][C:30]([Cl:33])=[CH:31][CH:32]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:20])[N:16]=[C:15]([N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1)[CH:14]=[CH:13]2)[CH2:8][OH:7])([CH3:38])([CH3:36])[CH3:37]

Participants

Conditions

Temperature: 50 °C

Procedure

To the solution of (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-morpholinoquinolin-6-yl)ethyl pivalate (15 mg) in THF/MeOH (1 mL/1 mL) was added sodium hydroxide solution (1.0 N, 1 mL). The mixture was heated at 50° C. for 16 hours and was diluted with water. The aqueous was extracted with ethyl acetate, and the organic phase was washed with brine, and dried over sodium sulfate. Concentration under reduced pressure gave (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-morpholinoquinolin-6-yl)ethanol (10 mg). LCMS-ESI+ (m/z): [M+H]+ calcd for C26H32ClN2O3: 454.2. Found: 455.3.

Workup

extractionThe aqueous was extracted with ethyl acetate
washthe organic phase was washed with brine
dry with materialdried over sodium sulfate
concentrationConcentration under reduced pressure

Sources & evidence

ORD record: ord-1bcb00341f394251b2994a6e3b4ed116
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296758B2

Reaction notes

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