Sodium borohydride → [9-(2,5-Dichlorobenzyl)-9H-beta-carbolin-3-yl]methanol

HRID 992561Notes

Reaction equation

HRID 992561 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]=2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 9908122methyl 9-(2,5-dichlorobenzyl)-9H-beta-carboline-3-carboxylate

Product 1

HCID 9928662[9-(2,5-Dichlorobenzyl)-9H-beta-carbolin-3-yl]methanolYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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%).

Workup

  1. customThe ethanol was evaporated
  2. customthe residue partitioned between 10% aqueous Na2CO3 (100 mL) and methylene chloride (100 mL)
  3. dry with materialThe organic phase was dried over MgSO4
  4. customevaporated
  5. customthe residue crystallized from ether

Sources & evidence

ORD record
ord-205e95ba63a941609dca897a7a81cf94
Source dataset
uspto-grants-2002_10
Patent number
US06469021B1

Reaction notes

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