2-Amino-2-methyl-1,3-propanediol → HCID 13817580, compound

HRID 1249493Notes

Reaction equation

HRID 1249493 reaction equation
[NH2:1][C:2]([CH3:7])([CH2:5][OH:6])[CH2:3][OH:4].[C:8](OCC)(=[O:12])[C:9]([CH3:11])=O>C(O)CCC>[CH3:11][C:9]1[C:8](=[O:12])[O:4][CH2:3][C:2]([CH3:7])([CH2:5][OH:6])[N:1]=1

Participants

4

Reactant 2

HCID 15312-Amino-2-methyl-1,3-propanediolHCID 12041Ethyl pyruvate

Product 1

HCID 13817580HCID 13817580, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

The results presented herein above and as shown in the schematic FIGS. 1 and 2 indicate that direct condensation of 2-amino-2-methyl-1,3-propanediol (1) with ethyl pyruvate in 1-butanol at reflux, followed by vacuum distillation, gives the 2,4-dimethyl-4-hydroxymethyl-1,3-oxazolidine-2-carboxylic acid ester of 5,6-dihydro-3,5-dimethyl-5-hydroxymethyl-1,4-oxazin-2-one (2). Evidence for the structure of the latter compound (2) is derived from elemental analysis, 1H NMR, IR and UV spectra, as well as chemical behavior. As described more specifically supra, the 1H NMR spectrum of 2 in deuteriochloroform showed four methyl singlets between 1.2 and 2.3 ppm, along with two very complex patterns between 3.3 and 4.7 ppm for the four --CH2 --O groups. The sharpness of the four methyl singlets suggests that 2 is mostly one of four possible diasteroisomers. The IR spectrum showed the bands characteristic of OH and/or NH stretching at 3000-3500, a very strong band at 1735 (C= O) and a band at 1635 cm-1 (C=N). The UV spectrum of 2 in 2-propanol solvent showed a maximum at 323 nm, characteristic of the oxazinone ring.

Workup

  1. temperatureat reflux
  2. distillationfollowed by vacuum distillation

Sources & evidence

ORD record
ord-0c570582f98c40579ce073b1617530d6
Source dataset
uspto-grants-1986_12
Patent number
US04632922

Reaction notes

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