Potassium Carbonate → Methyl 3-((1-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)methylthio)propanoate

HRID 1855059Notes

Reaction equation

HRID 1855059 reaction equation
I[CH2:2][C:3]12[CH2:10][CH2:9][C:6]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH:18]4[CH2:23][CH2:22][CH2:21][CH2:20]O4)[CH:12]=3)([CH2:7][CH2:8]1)[O:5][CH2:4]2.[SH:24][CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28].[C:31]([O-])([O-])=O.[K+].[K+]>C(#N)C.C(Cl)Cl>[O:17]([C:13]1[CH:12]=[C:11]([C:6]23[CH2:7][CH2:8][C:3]([CH2:2][S:24][CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])([CH2:10][CH2:9]2)[CH2:4][O:5]3)[CH:16]=[CH:15][CH:14]=1)[C:18]1[CH:31]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 18050Methyl 3-mercaptopropionateHCID 904096954-(Iodomethyl)-1-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octane

Product 1

HCID 90408240Methyl 3-((1-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)methylthio)propanoateYield 87%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(iodomethyl)-1-(3-phenoxyphenyl)-2-oxabicyclo[2.2.2]octane (7A; 41 mg, 0.098 mmol), methyl 3-mercaptopropanoate (21.14 μl, 0.195 mmol), and K2CO3 (135 mg, 0.976 mmol) in acetonitrile was stirred at rt for 2 days. The reaction was diluted with DCM (5 mL) and then filtered. The filtrate was concentrated in vacuo. The crude oil was purified by flash chromatography on SiO2 (0 to 30% EtOAc:hexanes) to afford the title compound (35 mg, 87% yield) as a clear oil. LCMS, [M+H]+=413.1.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe crude oil was purified by flash chromatography on SiO2 (0 to 30% EtOAc:hexanes)

Sources & evidence

ORD record
ord-da680c585211472fab0a9ab192c9395b
Source dataset
uspto-grants-2015_02
Patent number
US08962660B2

Reaction notes

Loading…