Acetic Acid → L 687414

HRID 1650776ノート

反応式

HRID 1650776 の反応式
[NH:1]([C@H:3]1[C@@H:7]([CH3:8])[CH2:6][N:5]([O:9]CC2C=CC=CC=2)[C:4]1=[O:17])N.C(O)(=O)C>C(O)C.[Pd]>[NH2:1][C@H:3]1[C@@H:7]([CH3:8])[CH2:6][N:5]([OH:9])[C:4]1=[O:17]

参加物

5

反応物 2

HCID 176Acetic AcidHCID 67790443HCID 67790443、化合物

生成物 1

HCID 125556L 687414収率 24.6%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

The hydrazine from step C (69 mg) was dissolved in ethanol (20 ml) and glacial acetic acid (5 ml) and the solution was hydrogenated at 50 psi for 2 h in the presence of palladium black (50 mg). The solution was filtered and further hydrogenated in the presence of platinum oxide (50 mg) at 50 psi for 1.5 h. The solution was filtered and the solvent evaporated to dryness. The residue was dissolved in water (10 ml) and applied to a column containing Dowex 50W-X8 (100-200 mesh, 2×2cm, H+ form). After washing the resin with water (3×15 ml) the product was eluted with dilute aqueous ammonia solution. The fractions containing the product were freeze dried to give cis-3-amino-1-hydroxy-4-methylpyrrolidin-2-one (9.4 mg). 1H NMR (250 MHz, D2O) δ3.91 (1H; d, J=8.09 Hz; CO--CH--N), 3.78 (1 H; dd, Jgem =10.0 Hz, J=7.OO Hz; CHHD AHBN), 3.23 (1H; dd, Jgem =10.1 Hz, J=3.0 Hz; CHAHBN ), 2.79-2.69 (1H; m; CHCH3), 1.10 (3H; d, J=7.22 Hz, CH3). Irradiation of the signal at 2.79ppm gave an NOE to the signals at 3.91 and 3.78, confirming the cis geometry. (m/e: theory, 130.0742; found, 130.0749).

後処理

  1. filtrationThe solution was filtered and further hydrogenated in the presence of platinum oxide (50 mg) at 50 psi for 1.5 h
  2. filtrationThe solution was filtered
  3. customthe solvent evaporated to dryness
  4. dissolutionThe residue was dissolved in water (10 ml)
  5. additioncontaining Dowex 50W-X8 (100-200 mesh, 2×2cm, H+ form)
  6. washAfter washing the resin with water (3×15 ml) the product
  7. washwas eluted with dilute aqueous ammonia solution
  8. additionThe fractions containing the product
  9. customdried

出典と根拠

ORDレコード
ord-7dda632fbc43419bba86c3da69f80f04
出典データセット
uspto-grants-1990_05
特許番号
US04925867

反応ノート

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