Sodium Cyanide → 2-amino-3-((tetrahydro-2H-pyran-2-yl) oxy)-2-(((tetrahydro-2H-pyran-2-yl)-oxy)-methyl)-propanenitrile
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
Procedure
5.6 g of the product of Stage 1 were introduced into 8 ml of ammonium hydroxide and the mixture was brought to about -5° C. 1.58 g of ammonium chloride and 1.23 g of sodium cyanide were added successively and the mixture was allowed to return to ambient temperature for about 40 minutes, then heated to 40° C.±5° C. with stirring overnight. The reaction medium was returned to ambient temperature and extraction was carried out 3 times with chloroform. The organic phase was washed with salt water and dried. After purification on silica with ethyl cycloacetate/triethylamine; 3/7 as eluant, 4.41 g of the expected product (pale yellow syrup) were obtained.
Workup
- customwas brought to about -5° C
- temperatureheated to 40° C.±5° C.
- customwas returned to ambient temperature
- extractionextraction
- washThe organic phase was washed with salt water
- customdried
- customAfter purification on silica with ethyl cycloacetate/triethylamine
Sources & evidence
- ORD record
- ord-3329cb6ab4874e91ae568167c20fe7d0
- Source dataset
- uspto-grants-1999_09
- Patent number
- US05958936
Reaction notes
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