Sodium Cyanide → HCID 86739779, compound

HRID 1153790Notes

Reaction equation

HRID 1153790 reaction equation
[ClH:1].[CH2:2]([O:9][C:10]1[C:11](=[O:20])[CH:12]=[C:13]([CH:16]([OH:19])[CH2:17][NH2:18])[O:14][CH:15]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:21]1([CH:27](C)[C:28](=O)[CH3:29])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[OH-].[Na+].[C-:34]#N.[Na+]>CO>[ClH:1].[CH2:2]([O:9][C:10]1[C:11](=[O:20])[CH:12]=[C:13]([CH:16]([OH:19])[CH2:17][NH:18][CH:29]([CH3:34])[CH2:28][CH2:27][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[O:14][CH:15]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 8929Sodium CyanideHCID 14798Sodium HydroxideHCID 977443-Phenyl-2-butanoneHCID 12311460HCID 12311460, compound

Product 1

HCID 86739779HCID 86739779, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 1-(5-Benzyloxy-4H-pyran-4-on-2-yl)-2-amino ethanol hydrochloride (1.94 g, 0.0065 m) and 3-phenyl-2-butanone (0.97 g, 0.0065 m) in methanol was added 65 ml of 0.1N NaOH followed by NaCN BH2 (0.25 g, 0.004 m). The mixture was stirred for 2 days at room temperature after concentration, chromatography on silica gel 60 (E. Merck) eluting with 5% CH3OH/CH2Cl2 saturated with NH3 afforded the desired product as its free base. The hydrochloride salt was prepared by dissolving in ethanol and adding aqueous HCl. Filtration of the solid upon attempted ether extraction gave a poor yield of the desired salt A; m.p. 205°-208° C.

Workup

  1. concentrationafter concentration, chromatography on silica gel 60 (E. Merck)
  2. washeluting with 5% CH3OH/CH2Cl2 saturated with NH3

Sources & evidence

ORD record
ord-fbf5bdbca6764d149171f22ef71d2ee4
Source dataset
uspto-grants-1984_12
Patent number
US04486446

Reaction notes

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