Triphenylphosphine → HCID 24878193, compound

HRID 902324Notes

Reaction equation

HRID 902324 reaction equation
[N:1]([CH2:4][C@H:5]1[CH2:14][CH2:13][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])[CH2:14][CH2:13]2

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 86609116HCID 86609116, compound

Product 1

HCID 24878193HCID 24878193, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-2-(azidomethyl)-8-(2,6-dichlorophenyl)-6-fluorochroman (0.26 g, 0.73 mmol) in tetrahydrofuran (10 mL) and water (1 mL) was added polymer-bound triphenylphosphine (˜3 mmol/g, 0.74 g, 2.2 mmol) and the reaction mixture stirred at room temperature for 2 days. The brown suspension was then filtered through celite, the filter cake washed with ethyl acetate (50 mL) and the combined filtrates concentrated under vacuum. The solvent was removed under vacuum. Chromatography with 0–10% methanol in methylene chloride plus 1% NH4OH afforded {[(R)-8-(2,6-dichlorophenyl)-6-fluoro-3,4-dihydro-2H-chromen-2-yl]methyl}amine as a colorless oil. The colorless oil was dissolved in ethyl acetate and made into its hydrochloride salt (0.18 g, 67%) as a white crystalline solid using excess ethereal hydrochloric acid, mp 190–192° C.; MS (ES) m/z 326.0 ([M+H]+); [α]D25=−4.39° (c 1% solution in MeOH).

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
  4. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-c9100c7959b2406284a99d8b68a0f0e2
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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