Ethanolamine → AGN-PC-009YWY

HRID 1499326Notes

Reaction equation

HRID 1499326 reaction equation
[CH:1]12[O:10][CH:7]([CH:8]=[CH:9]1)[CH:6]1[CH:2]2[C:3](=[O:12])O[C:5]1=[O:11].[CH2:13]([CH2:15][NH2:16])[OH:14]>CO>[OH:14][CH2:13][CH2:15][N:16]1[C:3](=[O:12])[CH:2]2[CH:6]([CH:7]3[O:10][CH:1]2[CH:9]=[CH:8]3)[C:5]1=[O:11]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 984843a,4,7,7a-Tetrahydro-4,7-epoxyisobenzofuran-1,3-dione

Product 1

HCID 12193800AGN-PC-009YWYYield 42%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

The anhydride, 4,10-dioxa-tricyclo[5.2.1.02,6]dec-8-ene-3,5-dione, (2.00 g, 12.0×10−3 mol) was suspended in 50 mL of MeOH and the mixture cooled to 0° C. A solution of ethanolamine (0.72 mL, 12.0×10−3 mol) in 20 mL of MeOH was added dropwise (10 min) and the resulting solution was stirred for 5 min at 0° C., then 30 min at room temperature and finally refluxed for 4 h. After cooling to room temperature the solvent was removed under reduced pressure, the white residue was dissolved in 150 mL of CH2Cl2 and washed with 3×100 mL of water. The organic layer was dried over MgSO4 and filtered. Removal of the solvent under reduced pressure furnished the desired product (1.04 g 5.0×10−3 mol, 42% yield) as white solid that was used for the next step without further purifications. An analytical sample was obtained by flash chromatography (CC, SiO2, 100% ethyl acetate, Rf(6)=0.26). m.p. 139-141° C. (dec). IR (neat): 3472, 1681, 1435, 1405, 1335, 1269, 1168, 1100, 1053, 1013, 959, 916, 875, 850, 807, 722, 705, 654 cm−1. 1H NMR (400.03 MHz, CDCl3, 298 K) δ 1.90 (bs, 1H, OH); 2.90 (s, 2H, CH), 3.69-3.72 (m, 2H, CH2), 3.76-3.78 (m, 2H, CH2), 5.28 (t, J=0.9 Hz, 2H, CH), 6.52 (t, J=0.9 Hz, 2H, CHvinyl). 13C{1H} NMR (100.59 MHz, CDCl3, 298 K) δ=41.77 (2C, NCH2), 60.18 (2C, OCH2), 47.50 (2C, CH), 81.04 (2C, CH), 136.60 (2C, CHvinyl), 176.97 (2C, C). Anal. Calcd. for C10H11NO4: C, 57.41; H, 5.30; N, 6.70. Found C, 57.16; H, 5.37; N, 6.62.

Workup

  1. temperature30 min at room temperature and finally refluxed for 4 h
  2. temperatureAfter cooling to room temperature the solvent
  3. customwas removed under reduced pressure
  4. dissolutionthe white residue was dissolved in 150 mL of CH2Cl2
  5. washwashed with 3×100 mL of water
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-8d07f22b1aec4ed68390d6ddee8b4ad6
Source dataset
uspto-grants-2015_12
Patent number
US09200104B2

Reaction notes

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