Sodium Cyanide → 2-amino-3-((tetrahydro-2H-pyran-2-yl) oxy)-2-(((tetrahydro-2H-pyran-2-yl)-oxy)-methyl)-propanenitrile

HRID 2288288Notes

Reaction equation

HRID 2288288 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9](=O)[CH2:10][O:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1.[OH-].[NH4+:20].[Cl-].[NH4+:22].[C-:23]#N.[Na+]>>[NH2:20][C:9]([CH2:8][O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)([CH2:10][O:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1)[C:23]#[N:22]

Participants

5

Reactant 4

HCID 8929Sodium CyanideHCID 14923Ammonium HydroxideHCID 25517Ammonium ChlorideHCID 110106602-Propanone, 1,3-bis[(tetrahydro-2H-pyran-2-yl)oxy]-

Product 1

HCID 218464882-amino-3-((tetrahydro-2H-pyran-2-yl) oxy)-2-(((tetrahydro-2H-pyran-2-yl)-oxy)-methyl)-propanenitrile

Procedure

5.6 g of the product obtained in Stage 1 above is introduced into 8 ml of ammonium hydroxide, the mixture is taken to about -5° C. and 1.58 g of ammonium chloride and 1.23 g of sodium cyanide are added successively and the reaction medium is left to rise to ambient temperature for about 40 minutes then heated at 40° C.±5° C. under agitation overnight. It is returned to ambient temperature and extraction is carried out 3 times with chloroform, the organic phase is washed with salt water and dried. After purification on silica, eluting with cyclohexane-ethyl acetate: 3-7 with 0.5% of triethylamine, 4.41 g of expected product (pale yellow syrup) is obtained.

Workup

  1. customis taken to about -5° C.
  2. waitthe reaction medium is left
  3. temperaturethen heated at 40° C.±5° C. under agitation overnight
  4. customis returned to ambient temperature
  5. extractionextraction
  6. washthe organic phase is washed with salt water
  7. customdried
  8. customAfter purification on silica
  9. washeluting with cyclohexane-ethyl acetate

Sources & evidence

ORD record
ord-9b4a24813fa3404c885cbffaab6aa1be
Source dataset
uspto-grants-2000_07
Patent number
US06087509

Reaction notes

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