Sodium Cyanide → HCID 18356482, compound

HRID 2223011Notes

Reaction equation

HRID 2223011 reaction equation
S(O[CH2:12][C@H:13]1[O:17][C:16](=[O:18])[NH:15][CH2:14]1)(C1C=CC(C)=CC=1)(=O)=O.[C-:19]#[N:20].[Na+]>CO.O>[C:19]([CH2:12][CH:13]1[O:17][C:16](=[O:18])[NH:15][CH2:14]1)#[N:20]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 13982966HCID 13982966, compound

Product 1

HCID 18356482HCID 18356482, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a stirring solution of (S)-5-tosyloxymethyl-1,3-oxazolidine-2-one (0.54 g, 1.99 mmol) in MeOH-water (15-3 mL) was added NaCN (0.39 g, 8.00 mmol) at room temperature and then heated to reflux for 4 h. After completion of the reaction, solvent in the reaction mixture was completely evaporated and the residue was purified by column chromatography employing EtOAc-hexane (70:30) as eluent to afford pure 5-cyanomethyl-1,3-oxazolidine-2-one in 70% yield. [α]26D=+4.5 (c 1.0, MeOH); IR (Neat) 3349, 2918, 2839, 2243, 1710, 1255, 1051 cm1; 1HNMR (200 MHz, CD3OD) δ 2.57 (d, 2H, J=6.6 Hz), 3.20-3.55 (m, 2H), 4.00-4.18 (m, 1H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 h
  3. customAfter completion of the reaction, solvent in the reaction mixture
  4. customwas completely evaporated
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-4f2587b3204a4086a9a62718da7c70d3
Source dataset
uspto-grants-2008_05
Patent number
US07374926B2

Reaction notes

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