Triphenylphosphine → (5S)-5-(Aminomethyl)-3-(5-chloropyridin-2-yl)-1,3-oxazolidin-2-one

HRID 2066810Notes

Reaction equation

HRID 2066810 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]([Cl:17])=[CH:13][N:12]=2)[CH2:6]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.O>[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]([Cl:17])=[CH:13][N:12]=2)[CH2:6]1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 59409901(5R)-5-(Azidomethyl)-3-(5-chloropyridin-2-yl)-1,3-oxazolidin-2-one2×

Product 1

HCID 59409907(5S)-5-(Aminomethyl)-3-(5-chloropyridin-2-yl)-1,3-oxazolidin-2-oneYield 87.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (5R)-5-(azidomethyl)-3-(5-chloropyridin-2-yl)-1,3-oxazolidin-2-one (2.22 g, INTERMEDIATE 9) and triphenylphosphine (3.44 g) was heated to 65° C. for 6 h in 444 ml of tetrahydrofuran and 56 ml of water. The sample was then cooled to room temperature, and concentrated in vacuo. The residue was purified via column chromatography on a Biotage Horizon 40M column eluting with 100% ethyl acetate (5 column volumes) to remove excess triphenylphosphine and triphenylphosphine oxide, followed by 100% methanol (5 column volumes), to provide the title compound (1.74 g, 87%). Mass spectrum (ESI) 228.1 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified via column chromatography on a Biotage Horizon 40M column
  3. washeluting with 100% ethyl acetate (5 column volumes)
  4. customto remove excess triphenylphosphine and triphenylphosphine oxide

Sources & evidence

ORD record
ord-eee8258b334946c480aed44416c31872
Source dataset
uspto-grants-2012_10
Patent number
US08293721B2

Reaction notes

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