Water → (1S)-2-(3,5-difluorophenyl)-1-[(2S)-oxiran-2-yl]ethylamine

HRID 1869723Notes

Reaction equation

HRID 1869723 reaction equation
[NH2:1][C@@H:2]([CH2:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[C:10]([F:15])[CH:9]=1)[C@H:3]([OH:6])[CH2:4]Cl.[OH-].[K+].O>C(O)C>[F:15][C:10]1[CH:9]=[C:8]([CH2:7][C@H:2]([NH2:1])[C@H:3]2[CH2:4][O:6]2)[CH:13]=[C:12]([F:14])[CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 9834600(2S,3S)-3-amino-1-chloro-4-(3,5-difluorophenyl)butan-2-ol

Product 1

HCID 86587041(1S)-2-(3,5-difluorophenyl)-1-[(2S)-oxiran-2-yl]ethylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

(1S,2S)-3-chloro-1-(3,5-difluorobenzyl)-2-hydroxypropylamine (EXAMPLE 17, 33mg, 0.14 mmol) and absolute ethanol (1.5 mL) are mixed. Potassium hydroxide (9.8 mg, 0.175 mmol) in absolute ethanol (0.5 mL) is added to this mixture and the resulting mixture is stirred at 20-25 deg for 30 min. At this time ESMS indicates formation of the product (MH+=200.1). Water (2 mL) is added and mixture is concentrated under reduced pressure to half the volume and then diluted with ethyl acetate (15 mL). The organic phase is separated and the aqueous phase is extracted with ethyl acetate (2×10 mL). The organic phases are combined, washed with saline and dried over anhydrous magnesium sulfate. The solvent is removed under reduced pressure to give the title compound, MH+=200.1.

Workup

  1. concentrationmixture is concentrated under reduced pressure to half the volume
  2. additiondiluted with ethyl acetate (15 mL)
  3. customThe organic phase is separated
  4. extractionthe aqueous phase is extracted with ethyl acetate (2×10 mL)
  5. washwashed with saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-9240df806bc548419676a55fce5cd333
Source dataset
uspto-grants-2009_12
Patent number
US07638646B2

Reaction notes

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