Triphenylphosphine → HCID 59701575, compound

HRID 902339Notes

Reaction equation

HRID 902339 reaction equation
[N:1]([CH2:4][C@H:5]1[CH:14]=[CH:13][C:12]2[C:7](=[C:8]([C:16]3[C:21]([Cl:22])=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:23])[CH:9]=[C:10]([F:15])[CH:11]=2)[O:6]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.O>[Cl:23][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]([Cl:22])[C:16]=1[C:8]1[CH:9]=[C:10]([F:15])[CH:11]=[C:12]2[C:7]=1[O:6][C@@H:5]([CH2:4][NH2:1])[CH:14]=[CH:13]2

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 86609126HCID 86609126, compound

Product 1

HCID 59701575HCID 59701575, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ((R)-2-azidomethyl-8-(2,6-dichloro-phenyl)-6-fluoro-2H-chromene (300 mg, 0.85 mmol) in tetrahydrofuran (10 mL) and water (0.5 mL) was added polymer-bound triphenylphosphine (˜3 mmol/g, 0.85 g, 2.6 mmol) and the reaction mixture stirred at room temperature for 43 hours. The brown suspension was then filtered through celite, the filter cake washed with ethyl acetate (50 mL) and the combined filtrates concentrated under vacuum. Chromatography with 0–10% methanol in methylene chloride plus 1% NH4OH afforded {[(2R)-8-(2,6-dichlorophenyl)-6-fluoro-2H-chromen-2-yl]methyl}amine as a colorless oil. The oil was dissolved in ethyl acetate and made into its hydrochlorde salt (83 mg, 27%) as a white crystalline solid using excess ethereal hydrochloric acid, mp 153–155° C.; [α]D25=+220.67° (c 1% solution in MeOH); MS (ES) m/z 324.0 ([M+H]+).

Workup

  1. filtrationThe brown suspension was then filtered through celite
  2. washthe filter cake washed with ethyl acetate (50 mL)
  3. concentrationthe combined filtrates concentrated under vacuum

Sources & evidence

ORD record
ord-733723109bc649e3bf225f8bdd1301c2
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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