Sodium borohydride → [9-(2,5-Dichlorobenzyl)-9H-beta-carbolin-3-yl]methanol
Reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:3]=1[CH2:4][N:5]1[C:17]2[CH:16]=[N:15][C:14]([C:18](OC)=[O:19])=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2.[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:3]=1[CH2:4][N:5]1[C:17]2[CH:16]=[N:15][C:14]([CH2:18][OH:19])=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of methyl 9-(2,5-dichlorobenzyl)-9H-β-carboline-3-carboxylate (13.05 g, 0.0339 mol), and sodium borohydride (3 g, 0.079 mol) was stirred and refluxed in anhydrous ethanol (200 mL) for 15 h. The ethanol was evaporated, and the residue partitioned between 10% aqueous Na2CO3 (100 mL) and methylene chloride (100 mL). The organic phase was dried over MgSO4, evaporated, and the residue crystallized from ether, affording the title product as an ivory-colored solid (11 g, 91%).