Sodium Carbonate → Methyl 4-(4-hydroxy-4-(2-hydroxyphenyl)piperidino)-2,2-diphenylbutyrate

HRID 279078

Reaction equation

Br[CH2:2][CH2:3][C:4]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:5]([O:7][CH3:8])=[O:6].[OH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:28]1([OH:34])[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[OH:34][C:28]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[OH:21])[CH2:29][CH2:30][N:31]([CH2:2][CH2:3][C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]([O:7][CH3:8])=[O:6])[CH2:32][CH2:33]1

Participants

Conditions

Temperature: 50 °C

Procedure

In 50 mL of anhydrous dimethylformamide were dissolved 2.24 g (6.7 mmol) of methyl 4-bromo-2,2-diphenylbutyrate and 1.30 g (6.7 mmol) of 4-(2-hydroxyphenyl)-4-piperidinol. To the resulting solution was added 1.07 g (10 mmol) of sodium carbonate, followed by stirring under heating at 50° C. for 35 hours. The residue obtained by distilling off the solvent under reduced pressure was dissolved in ethyl acetate, followed by washing with water and drying. The residue obtained by concentrating the solvent under reduced pressure was purified by chromatography on a silica gel column, whereby 870 mg (yield: 29.2%) of methyl 4-(4-hydroxy-4-(2-hydroxyphenyl)piperidino)-2,2-diphenylbutyrate was obtained.

Workup

customThe residue obtained
distillationby distilling off the solvent under reduced pressure
dissolutionwas dissolved in ethyl acetate
washby washing with water
customdrying
customThe residue obtained
concentrationby concentrating the solvent under reduced pressure
customwas purified by chromatography on a silica gel column

Sources & evidence

ORD record: ord-59483b05e9344a2b9c35e2788b5cb54c
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06362203B1

Linked notes

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