Water → (5S)-5-(Aminomethyl)-3-(5-bromopyrid-2-yl)-1,3-oxazolidin-2-one

HRID 747204Notes

Reaction equation

HRID 747204 reaction equation
[N:1]([CH2:4][C@@H:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][N:12]=2)[CH2:6]1)=[N+]=[N-].O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C>[NH2:1][CH2:4][C@@H:5]1[O:9][C:8](=[O:10])[N:7]([C:11]2[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][N:12]=2)[CH2:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 15341129(5R)-5-(Azidomethyl)-3-(5-bromopyrid-2-yl)-1,3-oxazolidin-2-one

Product 1

HCID 15341131(5S)-5-(Aminomethyl)-3-(5-bromopyrid-2-yl)-1,3-oxazolidin-2-oneYield 88.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(5R)-5-(Azidomethyl)-3-(5-bromopyrid-2-yl)-1,3-oxazolidin-2-one (5.60 g, 18.7 mM) was dissolved in acetonitrile:water (100:10 ml). Triphenylphosphine (5.42 g, 20.7 mM) was added. The reaction mixture was degassed and stirred at room temperature for 48 hours. The light yellow liquid was concentrated and the residue was purified by flash chromatography eluting with ethyl acetate then 6% methanol in ethyl acetate. Relevant fractions were combined to give the desired product as a light yellow solid (4.54 g).

Workup

  1. customThe reaction mixture was degassed
  2. concentrationThe light yellow liquid was concentrated
  3. customthe residue was purified by flash chromatography
  4. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-45356518230c4b9893d93d4687d99ff6
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

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