2-Amino-2-methyl-1,3-propanediol → Nsc57599

HRID 1025917Notes

Reaction equation

HRID 1025917 reaction equation
[NH2:1][C:2]([CH3:7])([CH2:5][OH:6])[CH2:3][OH:4].[C:8](=O)(OCC)[O:9]CC>C(O)C>[OH:4][CH2:3][C:2]1([CH3:7])[CH2:5][O:6][C:8](=[O:9])[NH:1]1

Participants

4

Reactant 2

HCID 15312-Amino-2-methyl-1,3-propanediolHCID 7766Diethyl Carbonate

Product 1

HCID 245546Nsc57599

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A Dean-Stark trap was fitted to a flask containing 2-amino-2-methyl-1,3-propanediol (21.62 g, 205.6 mmol) suspended in diethyl carbonate (40 ml, 330 mmol). The suspension was heated to 150° C. for 6 h, during which time approximately 12 ml of ethanol was distilled. The solution was cooled to RT overnight, and the resulting crystals were filtered and washed with cold ethanol. The crude material (˜90% purity) was used without further purification (24.82 g, 189.0 mmol, 92%). 1H NMR (CDCl3, 400 MHz) δ 1.36 (s, 3H), 2.2 (br s, 1H), 3.57 (m, 2H), 4.06 (d, 1H, J=8.8 Hz), 4.33 (d, 1H, J=8.8 Hz), 5.2 (br s, 1H). LRMS (ESI/APCI): 132 [M+H]+.

Workup

  1. customA Dean-Stark trap was fitted to a flask
  2. distillationwas distilled
  3. filtrationthe resulting crystals were filtered
  4. washwashed with cold ethanol
  5. customThe crude material (˜90% purity) was used without further purification (24.82 g, 189.0 mmol, 92%)

Sources & evidence

ORD record
ord-bf0010566b8d486d86ece8fcb3a3a214
Source dataset
uspto-grants-2014_05
Patent number
US08729112B2

Reaction notes

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