Piperidine → HCID 58537209, compound

HRID 1804487Notes

Reaction equation

HRID 1804487 reaction equation
[C:1]1([S:7]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:14][O:15][CH:16]([O:19][CH3:20])[CH:17]=O.N1CCCCC1>C(#N)C>[CH3:14][O:15][CH:16]([O:19][CH3:20])/[CH:17]=[C:9](/[S:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:8])\[C:10]([O:12][CH3:13])=[O:11]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 84191Methyl (benzenesulfinyl)acetateHCID 162650Acetaldehyde, 2,2-dimethoxy-

Product 1

HCID 58537209HCID 58537209, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl 2-(phenylsulfinyl)acetate (1 g, 5.04 mmol), 2,2-dimethoxyacetaldehyde (3.15 ml, 10.09 mmol) and piperidine (0.999 ml, 10.09 mmol) in acetonitrile (20 ml) was heated to 60° C. for 18 hr. After cooling to rt, the volatiles were removed in vacuo and the residue was chromatographed on a 5×12 cm silica gel column, eluting with a 0-40% EtOAc/Hex gradient. The pure fractions were concentrated to afford (E)-methyl 4,4-dimethoxy-2-(phenylsulfinyl)but-2-enoate (1.42 g, 4.99 mmol, 99% yield) as a light yellow oil. HPLC retention time=1.23 minutes (PHENOMENEX® Luna 4.6×30 mm S-5 ODS column) eluting with 10-90% aqueous methanol+0.1% TFA over a 2 minute gradient. MS: (M+Na)=307.06. 1H NMR (500 MHz, chloroform-d) δ ppm 3.40 (s, 3H), 3.41 (s, 3H), 3.69 (s, 3H), 5.71 (d, J=7.2 Hz, 1H), 7.07 (d, J=6.6 Hz, 1H), 7.48 (m, 3H), 7.66 (m, 2H).

Workup

  1. temperatureAfter cooling to rt
  2. customthe volatiles were removed in vacuo
  3. customthe residue was chromatographed on a 5×12 cm silica gel column
  4. washeluting with a 0-40% EtOAc/Hex gradient
  5. concentrationThe pure fractions were concentrated

Sources & evidence

ORD record
ord-2a73eee30c9c4d85bfb140c931c9c650
Source dataset
uspto-grants-2013_01
Patent number
US08354398B2

Reaction notes

Loading…