Carbon Dioxide → (S)-2-amino-4-methylpentane-1,4-diol

HRID 1916045Notes

Reaction equation

HRID 1916045 reaction equation
[OH:1][C:2]([CH3:11])([CH3:10])[CH2:3][C@H:4]1[CH2:8][O:7]C(=O)[NH:5]1.[OH-].[Ba+2].[OH-].C(O)C.C(=O)=O>O>[NH2:5][C@@H:4]([CH2:3][C:2]([CH3:11])([OH:1])[CH3:10])[CH2:8][OH:7]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 702EthanolHCID 6093286Barium hydroxideHCID 11321109(S)-4-(2-Hydroxy-2-methylpropyl)oxazolidin-2-one

Product 1

HCID 55285389(S)-2-amino-4-methylpentane-1,4-diolYield 83.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (4S)-4-(2-hydroxy-2-methylpropyl)-1,3-oxazolidin-2-one (1.0 g, 6.28 mmol), barium hydroxide (3.2 g, 18.8 mmol), ethanol (50 mL) and water (50 mL) was heated to reflux for 4 hours. See Gauthier et al., 2008, Bioorg. Med. Chem. Lett., 18:923-928. After cooling, dry ice (5.5 g, 125.6 mmol) was added and the mixture was stirred vigorously overnight. The suspension was then filtered over CELITE®, rinsing with ethanol. The filtrate was diluted with toluene and evaporated to dryness, yielding crude (S)-2-amino-4-methylpentane-1,4-diol (0.7 g) which was used without further purification in the next step.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 hours
  3. temperatureAfter cooling
  4. filtrationThe suspension was then filtered over CELITE®
  5. washrinsing with ethanol
  6. additionThe filtrate was diluted with toluene
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-8a51697c579443c890bb0e9251a46ae9
Source dataset
uspto-grants-2013_12
Patent number
US08618096B2

Reaction notes

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