Sodium → 5-Hydroxymethyl-4-methoxymethyl-beta-carboline-3-carboxylic acid ethyl ester

HRID 845235Notes

Reaction equation

HRID 845235 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH2:19][O:20][CH3:21])=[C:15]([CH2:22][O:23]C(=O)C)[CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2].[Na]>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[C:18]=1[CH2:19][O:20][CH3:21])=[C:15]([CH2:22][OH:23])[CH:14]=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 5360545SodiumHCID 138503625-Acetoxymethyl-4-methoxymethyl-beta-carboline-3-carboxylic acid ethyl ester

Product 1

HCID 138503635-Hydroxymethyl-4-methoxymethyl-beta-carboline-3-carboxylic acid ethyl esterYield 94.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Acetoxymethyl-4-methoxymethyl-beta-carboline-3-carboxylic acid ethyl ester (7.9 g) is taken up in a solution of sodium (1.4 g) in ethanol (100 ml) and left for 4 days at +4° C. The solution is concentrated, taken up in abundant ethyl acetate, washed alkali-free with water, dried with sodium sulfate and evaporated in a vacuum. By treatment with ethanol the residue yields 6.6 g of the title compound as colorless crystals with a melting point of 139°-140° C.

Workup

  1. concentrationThe solution is concentrated
  2. washwashed alkali-free with water
  3. dry with materialdried with sodium sulfate
  4. customevaporated in a vacuum

Sources & evidence

ORD record
ord-881067ecffc546c4ab404855bc317eb1
Source dataset
uspto-grants-1988_07
Patent number
US04757070

Reaction notes

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