Triphenylphosphine → HCID 15942618, compound

HRID 902327Notes

Reaction equation

HRID 902327 reaction equation
[N:1]([CH2:4][C@H:5]1[CH:14]=[CH:13][C:12]2[C:7](=[C:8]([C:15]3[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=3[Cl:22])[CH:9]=[CH:10][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:22][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]([Cl:21])[C:15]=1[C:8]1[CH:9]=[CH:10][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 86609117HCID 86609117, compound

Product 1

HCID 15942618HCID 15942618, compoundYield 90.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2R)-2-azidomethyl-8-(2,6-dichloro-phenyl)-2H-chromene (120 mg, 0.361 mmol) in tetrahydrofuran (5 mL) and water (0.5 mL) was added polymer-bound triphenylphosphine (˜3 mmol/g, 0.361 g, 1.084 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 reduced pressure to afford a yellow syrup. Purification by flash chromatography using a solvent gradient of 0 to 5% ammonia saturated methanol solution in dichloromethane gave 100 mg (90%) of {[(2R)-8-(2,6-dichlorophenyl)-2H-chromen-2-yl]methyl}amine as a colorless syrup. The product was dissolved in 2-propanol (1 mL) and diethyl ether (2 mL), a solution of hydrogen chloride (1.0 M in diethyl ether, 0.326 mL, 0.326 mmol) was added followed hexane (7 mL). The resulting white precipitate was filtered to afford 100 mg (80%) of {[(2R)-8-(2,6-dichlorophenyl)-2H-chromen-2-yl]methyl}amine hydrochloride as an off-white solid.

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 reduced pressure
  4. customto afford a yellow syrup
  5. customPurification by flash chromatography

Sources & evidence

ORD record
ord-0a89d42900864008a3944f5fbdf2c921
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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