HCID 11736760, compound → HCID 15875322, compound

HRID 1016709Notes

Reaction equation

HRID 1016709 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([O:15][C:16](=[O:18])[CH3:17])[CH2:12][CH:13]=[CH2:14])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]>CCO.O=[Pt]=O>[C:16]([O:15][CH:11]([C:8]1[CH:7]=[CH:6][C:5]([O:4][C:1](=[O:3])[CH3:2])=[CH:10][CH:9]=1)[CH2:12][CH2:13][CH3:14])(=[O:18])[CH3:17]

Participants

4

Reactant 1

HCID 11736760HCID 11736760, compound

Product 1

HCID 15875322HCID 15875322, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

1.0 g (4 mmol) diacetate 9 is dissolved in 19 ml EtOH and hydrogenated over 50 mg PtO2. The catalyst is removed by filtration over Celite and the solvent is evaporated. Flash chromatography of the crude product gave 0.92 g (91% by weight) of compound 15 in the form of a yellowish oil having the following 1H NMR (CDCl3) values: 0.92 g (t, J=7.0, CH3); 1.15-1.45 (m, 2H, CH2); 1.62-2.00 (m, 2H, CH2); 2.05 (s, CH3); 2.30 (s, CH3); 5.74 (t, J=7.0, CH ); 7.06 J=9.0, 2 aromatic H); 7.34 (d, J=9.0, 2 aromatic H); 7.34 (d, J=9.0, 2 aromatic H). MS: 250 (2, [M+]), 208 (19), 165 (32), 123 (68), 43 (100).

Workup

  1. customThe catalyst is removed by filtration over Celite
  2. customthe solvent is evaporated

Sources & evidence

ORD record
ord-178a3544997c4be08f1d5e609a1d2ef1
Source dataset
uspto-grants-2002_11
Patent number
US06476252B1

Reaction notes

Loading…