Piperidine → (+/-)-3-(4-Methoxyphenylsulfanyl)-2-methyl-7-phenylheptanoic acid

HRID 1107184Notes

Reaction equation

[CH3:1]/[C:2](=[CH:6]\[CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)/[C:3]([OH:5])=[O:4].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([SH:25])=[CH:21][CH:20]=1.N1CCCCC1>>[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([S:25][CH:6]([CH2:7][CH2:8][CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:2]([CH3:1])[C:3]([OH:5])=[O:4])=[CH:21][CH:20]=1

Participants

Reactant 3

HCID 8082Piperidine

HCID 127654-Methoxybenzenethiol

HCID 18790128(E)-2-Methyl-7-phenyl-hept-2-enoic acid

Product 1

HCID 18790075(+/-)-3-(4-Methoxyphenylsulfanyl)-2-methyl-7-phenylheptanoic acidYield 25.1%

Conditions

Temperature: 85 °C

Procedure

(E)-2-Methyl-7-phenyl-hept-2-enoic acid (2.2 g, 10 mmol), 4-methoxybenzenethiol (2.8 g, 20 mmol) and piperidine (0.1 mL, 1 mmol) are combined and heated at 85° C. for 12 hours. The reaction is cooled and purified by gradient elution chromatography (silica, 35 to 100% ether in petroleum ether) to yield (±)-3-(4-Methoxyphenylsulfanyl)-2-methyl-7-phenylheptanoic acid (0.9 g, 25%) as a 50/50 mixture of diastereomers: 1H NMR (300 MHz, CDCl3) δ 7.39-7.34 (m, 2H), 7.29-7.25 (m, 2H), 7.20-7.11 (m, 3H), 6.81 (m, 2H), 3.79 (s, 1.5H), 3.78 (s, 1.5H), 3.30-3.16 (m, 1H), 2.70-2.54 (m, 3H), 1.72-1.40 (m, 6H), 1.28 (d, J=7.0 Hz, 1.5H), 1.22 (d, J=7.0 Hz, 1.5H); MS (FAB) m/e 359 (M+H)+.

Workup

temperatureThe reaction is cooled
custompurified by gradient elution chromatography (silica, 35 to 100% ether in petroleum ether)

Sources & evidence

ORD record: ord-98ed69ea77da4e819754ed67df328e29
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06057369

Reaction notes

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