98988-21-7Relevant articles and documents
A Convenient Total Synthesis of (+/-)-Bharatamine and (+/-)-Isobharatamine
Patil, Sharadbala D.,Mali, R. S.
, p. 360 - 362 (2007/10/02)
N,N-Dimethylbenzylamine (1) on lithiation with n-butyllithium followed by reaction with paraformaldehyde gives the 2-hydroxymethyl derivative (2). 2 on successive reactions with ClCOOEt, KCN and alc.KOH followed by cyclisation furnishes isochroman-3-one (3).Condensation of 3 with phenylethylamines (4a) and (4b), followed by cyclisation (PCl5), reduction (NaBH4), and debenzylation (EtOH-HCl) gives (+/-)-bharatamine (6c) and (+/-)-3-hydroxy-4-methoxy-5,6,13,13a-tetrahydro-8H-dibenzoquinolizine (isobharatamine, 6d), respectively in high yields.