Ammonium Hydroxide → 4-{[(2R)-3-Amino-2-hydroxypropyl]oxy}benzonitrile

HRID 411540Notes

Reaction equation

HRID 411540 reaction equation
[O:1]1[CH2:3][C@@H:2]1[CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1.[NH4+:14].[OH-]>C(O)(C)C>[NH2:14][CH2:3][C@@H:2]([OH:1])[CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 6934186(R)-4-(Oxiran-2-ylmethoxy)benzonitrile

Product 1

HCID 300720964-{[(2R)-3-Amino-2-hydroxypropyl]oxy}benzonitrileYield 91%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4-[(2R)-Oxiranylmethoxy]benzonitrile (see step (i) above; 14.65 g, 83.6 mmol) was mixed with NH4OH (conc., 64 mL) and 87 mL of isopropanol. The mixture was stirred at rt for 18 h. The reaction mixture was then filtered and evaporated to give 14.6 g (91%) of the sub-title compound as a white solid.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. customevaporated

Sources & evidence

ORD record
ord-dab5659829564b2dac29ccc1ae92c8e7
Source dataset
uspto-grants-2003_05
Patent number
US06559162B2

Reaction notes

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