Tetrahydrofuran → HCID 67034016, compound

HRID 539072Notes

Reaction equation

HRID 539072 reaction equation
Cl.[NH2:2][C@@H:3]([C:6]1[CH:7]=[N:8][CH:9]=[CH:10][CH:11]=1)[CH2:4][OH:5].[OH-].[K+].C1C[O:17][CH2:16]C1.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>O>[N:8]1[CH:9]=[CH:10][CH:11]=[C:6]([C@H:3]2[CH2:4][O:5][C:16](=[O:17])[NH:2]2)[CH:7]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 94429TriphosgeneHCID 67033338HCID 67033338, compound

Product 1

HCID 67034016HCID 67034016, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-2-amino-2-(pyridin-3-yl)ethanol hydrochloride (0.255 g, 1.46 mmol) in water (2 mL) was added potassium hydroxide (0.573 g, 10.2 mmol) and the reaction stirred until complete dissolution occurred, followed by addition of THF (3 mL) and the reaction cooled to 0° C. To the reaction was next added triphosgene (0.433 g, 1.46 mmol) and the reaction allowed to warm up to ambient temperature and stirred for 18 hours. The reaction was concentrated and the adjusted to about pH 8 with 3N NaOH, and concentrated. The residue was purified on silica gel (2-10% 7N ammonia in MeOH in DCM) to provide (S)-4-(pyridin-3-yl)oxazolidin-2-one (0.054 g, 23% yield) as a beige solid.

Workup

  1. temperatureto warm up to ambient temperature
  2. stirringstirred for 18 hours
  3. concentrationThe reaction was concentrated
  4. concentrationconcentrated
  5. customThe residue was purified on silica gel (2-10% 7N ammonia in MeOH in DCM)

Sources & evidence

ORD record
ord-ac38d47e62524d32b6e107666a58d0b0
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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