Triphenylphosphine → (5S)-5-(aminomethyl)-3-(4-iodophenyl)-1,3-oxazolidin-2-one

HRID 747207Notes

Reaction equation

HRID 747207 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]([I:17])=[CH:13][CH:12]=2)[CH2:6]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C.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]([I:17])=[CH:13][CH:12]=2)[CH2:6]1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 59749482(5R)-5-(azidomethyl)-3-(4-iodophenyl)-1,3-oxazolidin-2-one

Product 1

HCID 59749453(5S)-5-(aminomethyl)-3-(4-iodophenyl)-1,3-oxazolidin-2-oneYield 81.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

(5R)-5-(Azidomethyl)-3-(4-Iodophenyl)-1,3-oxazolidin-2-one (8.0 g, 23.2 mmol) was dissolved in acetonitrile (160 ml) and water (16 ml). Triphenylphosphine (7.3 g, 27.9 mmol) was added and the mixture stirred at room temperature overnight. The volatiles were removed by concentration in vacuo, and the resulting residue partitioned between water (200 ml) and dichloromethane (200 ml). The aqueous layer was extracted with dichloromethane (2×200 ml) and dried over sodium sulfate. The crude material was purified by flash chromatography on silica gel with 0-10% methanol in dichloromethane as the eluent giving the desired product (6.0 g).

Workup

  1. customThe volatiles were removed by concentration in vacuo
  2. customthe resulting residue partitioned between water (200 ml) and dichloromethane (200 ml)
  3. extractionThe aqueous layer was extracted with dichloromethane (2×200 ml)
  4. dry with materialdried over sodium sulfate
  5. customThe crude material was purified by flash chromatography on silica gel with 0-10% methanol in dichloromethane as the eluent

Sources & evidence

ORD record
ord-9e7136d470a34d3e8cc4abe079542255
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

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