Sodium → HCID 20155386, compound

HRID 2413719Notes

Reaction equation

HRID 2413719 reaction equation
[Na].[CH2:2]([O:9][C:10]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:11]=1[C:12]1[C:13]([CH2:35][O:36][CH3:37])=[C:14]([CH:33]=[CH2:34])[N:15]=[CH:16][C:17]=1[N:18]2S(C1C=CC(C)=CC=1)(=O)=O)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CO>[CH2:2]([O:9][C:10]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:11]=1[C:12]1[C:13]([CH2:35][O:36][CH3:37])=[C:14]([CH:33]=[CH2:34])[N:15]=[CH:16][C:17]=1[NH:18]2)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 5360545SodiumHCID 20155385HCID 20155385, compound

Product 1

HCID 20155386HCID 20155386, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 0.23 g of sodium in 10 ml of methanol is added drop by drop with stirring to a suspension of 0.5 g of 5-benzyloxy-4-methoxymethyl-9-tosyl-3-vinyl-beta-carboline in 20 ml of methanol. After 72 hours of stirring at room temperature, it is evaporated to dryness and the residue is chromatographed over silica gel with dichloromethane/ethanol=10/1 as eluant. 0.135 g of 5-benzyloxy-4-methoxymethyl-3-vinyl-beta-carboline with a melting point of 183°-185° C. is obtained.

Workup

  1. customit is evaporated to dryness
  2. customthe residue is chromatographed over silica gel with dichloromethane/ethanol=10/1 as eluant

Sources & evidence

ORD record
ord-1cca7dd45f3649318356876b1c93e809
Source dataset
uspto-grants-1988_01
Patent number
US04719210

Reaction notes

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