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

HRID 1743732Notes

Reaction equation

HRID 1743732 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 (14.65 g, 83.6 mmol; prepared as described in international patent application WO 99/31100) was mixed with conc. NH4OH (64 mL) and 87 mL of isopropanol. The mixture was stirred at r.t for 18 h. The reaction mixture was filtered and the filtrate evaporated to give 14.6 g (91%) of the sub-title compound.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-2898c09fcc9b474dbeffd4f6f392d00f
Source dataset
uspto-grants-2006_03
Patent number
US07012074B2

Reaction notes

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