Toluene → Dichloromethane methanol ammonium hydroxide

HRID 23203

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][N:11](C)[CH2:12][CH2:13][CH2:14][NH2:15])=[CH:9][C:4]=2[O:3][CH2:2]1.[C:17]([O:21][CH2:22][CH3:23])(=[O:20])[CH:18]=[O:19].C1(C)C=CC=CC=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH2:45]([Cl:47])[Cl:46]>>[CH2:45]([Cl:47])[Cl:46].[CH3:2][OH:1].[OH-:19].[NH4+:11].[CH2:22]([O:21][C:17](=[O:20])[CH2:18][NH:15][CH2:14][CH2:13][CH2:12][NH:11][CH2:10][C:8]1[CH:7]=[CH:6][C:5]2[O:1][CH2:2][O:3][C:4]=2[CH:9]=1)[CH3:23]

Participants

Reactant 5

HCID 1140Toluene

HCID 6344Dichloromethane

HCID 70211Ethyl oxoacetate

HCID 5049666Sodium triacetoxyborohydride

HCID 22488891N-(1,3-benzodioxol-5-ylmethyl)-N-methyl-1,3-propanediamine

Product 2

HCID 21896990Dichloromethane methanol ammonium hydroxide

HCID 697424072-[[3-[(1,3-Benzodioxol-5-ylmethyl)amino]propyl]amino]acetic acid ethyl ester

Procedure

To N-(1,3-benzodioxol-5-ylmethyl)-N-methyl-1,3-propanediamine (33 g, 0.15 mol) in CH2Cl2 (500 mL) was added ethyl glyoxalate (30 mL of a 50% toluene solution, 0.15 mol) and sodium triacetoxyborohydride (40 g, 0.19 mol). After stirring for 4 hours, the reaction was washed with aqueous potassium carbonate and the solvent removed in vacuo. Chromatography on silica with CH2Cl2/MeOH/ammonium hydroxide gave 14 g of 2-[[3-[(1,3-benzodioxol-5-ylmethyl)amino]propyl]amino]acetic acid ethyl ester, a compound of formula (Y10).

Workup

washthe reaction was washed with aqueous potassium carbonate
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-47af93b00e774df4bf87003cb99adca8
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06849739B2

Linked notes

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