Triphenylphosphine → HCID 9931159, compound

Participants

Reaction Steps

A catalytic amount of tetrakis(triphenylphosphine)palladium (5.0 mg, 4.33 μmol) was added to a stirred solution of the Alloc-protected carbinolamine 23 (88 mg, 0.17 mmol), triphenylphosphine (2.27 mg, 8.65 μmol) and pyrrolidine (13 mg, 0.18 mmol) in CH2Cl2 (15 mL). After 2 hours stirring at room temperature under a nitrogen atmosphere, TLC (80% EtOAc/Petroleum Ether) revealed the complete consumption of starting material. The solvent was evaporated in vacuo and the crude residue was purified by flash chromatography (60% EtOAc/Petroleum Ether) to afford the novel PBD (SJG-245) as a colourless glass (54 mg, 77%) which was repeatedly evaporated in vacuo with CHCl3 in order to provide the N10-C11 imine form 24: 1H NMR (270 MHz, CDCl3) (imine) δ7.80 (d, 1H, J=4.03 Hz, HC═N), 7.50 (s, 1Harom), 7.45-7.26 (m, 5Harom), 6.91 (br s, 1H, NCH═CCH2OC2CH3), 6.83 (s, 1Harom), 5.21-5.12 (m, 2H, PhCH2O), 3.94 (s, 3H, OCH3), 3.73 (s, 3H, CO2CH3), 3.23 (s, 2H, NCH═CCH2CO2CH3), 3.15 (m, 2H, NCH═CCH2CO2CH3CH2); 13C NMR (67.8 MHz, CDCl3) (imine) δ170.7 (CO2CH3), 162.7 (HC═N), 161.4 (NC═O), 150.9 (Carom), 148.1 (Carom), 140.1 (Carom), 136.0 (Carom), 128.7, 128.2 and 127.3 (BnC—Harom), 127.3 (NCH═CCH2CO2CH3), 119.2 (Carom), 117.5 (NCH═CCH2CO2CH3), 111.8 (C—Harom), 111.5 (C—Harom), 70.8 (PhCH2O), 56.2 (OCH3), 53.8 (NCHHC═N), 52.0 (CO2CH3), 37.4 (NCH═CCH2CO2CH3), 33.6 (NCH═CCH2CO2CH3CH2)

Provenance & Evidence