(+-)-Pantolactone → HCID 59752169, compound

HRID 877703Notes

Reaction equation

HRID 877703 reaction equation
[OH:1][CH:2]1[C:6]([CH3:8])([CH3:7])[CH2:5][O:4][C:3]1=O.[C:10]1([CH2:16][NH2:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(OCC)(=O)C>[CH2:16]([N:17]1[CH2:5][C:6]([CH3:8])([CH3:7])[CH:2]([OH:1])[C:3]1=[O:4])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 989(+-)-PantolactoneHCID 6101p-Toluenesulfonic acidHCID 7504Benzylamine

Product 1

HCID 59752169HCID 59752169, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
210 °C

Procedure

A mixture of 3-hydroxy-4,4-dimethyldihydrofuran-2(3H)-one (4.5 g, 34.6 mmol), phenylmethanamine (5.66 mL, 51.9 mmol) and p-toluenesulfonic acid (0.595 g, 3.46 mmol) was sealed in a reaction vial and heated in microwave at 210° C. for 3 h. The mixture was diluted with ethyl acetate (300 mL). The organic layer was washed with 1N HCl (30 mL) three times, brine (20 mL), dried and concentrated. The residue was purified via silica gel chromatography, eluting with 20-50% ethyl acetate in hexanes, to give the title compound as a yellow oil (3.4 g, 45% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ 7.37-7.29 (m, 3H), 7.26-7.22 (m, 2H), 4.55-4.36 (m, 2H), 4.02 (s, 1H), 3.37 (br. s., 1H), 3.00-2.83 (m, 2H), 1.18 (s, 3H), 0.96 (s, 3H); MS (ES+) m/z: 219.1, 220.1 (M+H); LC retention time: 2.83 min (analytical HPLC Method I).

Workup

  1. customwas sealed in a reaction vial
  2. washThe organic layer was washed with 1N HCl (30 mL) three times, brine (20 mL)
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified via silica gel chromatography
  6. washeluting with 20-50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-6229e56117ac4df790f5d222dd1a6bd5
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

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