Formaldehyde → 6-Benzyloxy-4-methoxymethyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid isopropyl ester

HRID 1940526Notes

Reaction equation

HRID 1940526 reaction equation
[CH:1]([O:4][C:5](=[O:29])[CH:6]([NH2:28])[CH:7]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:18]=2)[NH:13][CH:12]=1)[CH2:8][O:9][CH3:10])([CH3:3])[CH3:2].[CH2:30]=O>C1(C)C(C)=CC=CC=1>[CH:1]([O:4][C:5]([CH:6]1[CH:7]([CH2:8][O:9][CH3:10])[C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:18]=3)[NH:13][C:12]=2[CH2:30][NH:28]1)=[O:29])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 140762742-Amino-3-(5-benzyloxyindol-3-yl)-4-methoxybutyric acid isopropyl ester

Product 1

HCID 110800626-Benzyloxy-4-methoxymethyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid isopropyl esterYield 65%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

A solution is prepared from 3.8 g of 2-amino-3-(5-benzyloxyindol-3-yl)-4-methoxybutyric acid isopropyl ester (10 mmol) in 80 ml of xylene and added dropwise to a suspension of 360 mg of paraformaldehyde in 60 ml of xylene heated for 45 minutes to 100° C. The mixture is then refluxed for 2 hours on a water trap. After concentration, the residue is chromatographed over silica gel with methylene chloride:acetone=1:1 as the eluent, yielding 2.5 g of 6-benzyloxy-4-methoxymethyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid isopropyl ester (65% yield as an oil); or

Workup

  1. temperatureheated for 45 minutes to 100° C
  2. temperatureThe mixture is then refluxed for 2 hours on a water trap
  3. concentrationAfter concentration
  4. customthe residue is chromatographed over silica gel with methylene chloride

Sources & evidence

ORD record
ord-5b0137fd555a42eda57755ea0e8821c1
Source dataset
uspto-grants-1997_12
Patent number
US05700808

Reaction notes

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