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A solution of 4a (6.25g , 31 mmol) in DCM (200 mL) was added to 35 (1.0 g, 4.97 mmol). To the resulting mixture was added NaBH(OAc)3 (9.86 g, 47 mmol) in two portions and the reaction stirred for 18 h at RT. The reaction was washed with a solution 5percent NaHC03 (100 mL). The organic phase was dried (Na2S04) and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel eluting with DCM/ 3.5percent MeOH (containing 10percent NH40H) to afford 6.8 g (46percent) of 36a as a viscous liquid: MS (ES+) m/z 436 (M + H)+.
A 25 mL 3-neck flask equipped with stir bar, addition funnel, N2 inlet tube and reflux condenser was charged with 4a (l.Og, 4.94 mmol) and (dry) toluene (4 mL) and cooled to 0 C. Trimethylaluminum (2.5 mL of a 2.0 M toluene solutionn, 5.0 mmol) was added dropwise, then allowed to warm to RT. 2,4-Dimethyl-nicotinic acid ethyl ester (80, 0.93 g, 5.2 mmol) in toluene (1 mL) was added dropwise then heated at 120 C for 18 h. The reaction mixture was cooled in an ice bath and MeOH (2 mL) was added. The mixture was brought to RT, heated at reflux for 10 min then recooled to RT. The mixture was filtered through a CELITE pad. The filtrate was washed with brine, dried (MgS04) then concentrated in vacuo. The crude product was purified by flash chromatography on silica eluting with 7.5% MeOH (containing 2% NH40H) / DCM to afford 1.17 g, (71%) of 81 as a pale yellow liquid: ms (ES+) m/z 336 (M+H)+.
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