Sodium Hydroxide → HCID 15884728, compound

Participants

Reaction Steps

To a solution of 2-methoxymethyl-5-(2-methoxyphenyl)-tetrahydropyrrole (226 mg, 1.02 mmol) in CH2Cl2 was added NaOAc (88 mg, 1.07 mmol), N-phthalimidoacetaldehyde (203 mg, 1.07 mmol) and NaB(OAc)3H (326 mg, 1.54 mmol) and the resulting suspension was stirred at ambient temperature for 17 hours. H2O was added followed by 1N NaOH until pH was 10, the aqueous layer was extracted with CHCl3 (×4), and the combined organic layers were washed with brine, dried over MgSO4 and evaporated in vacuo. The crude product was purified by silica gel flash chromatography (5% MeOH-0.5% NH3.H2O-94.5% CH2Cl2) to afford the title compound as a yellow oil (348 mg, 86%). MS m/z: 395 (M+H)

Provenance & Evidence