Triphenylphosphine → WAY-261240

HRID 902306Notes

Reaction equation

HRID 902306 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[O:17][C@@H:16]([CH2:19][N:20]=[N+]=[N-])[CH2:15][CH2:14]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[O:17][C@@H:16]([CH2:19][NH2:20])[CH2:15][CH2:14]2

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 86609105HCID 86609105, compound

Product 1

HCID 17747578WAY-261240Yield 82.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {[(2R)-8-(2,6-dichlorophenyl)-3,4-dihydro-2H-chromen-2-yl]methyl}azide (0.21 g, 0.628 mmol) in tetrahydrofuran (10 mL) and water (1 mL) was added polymer-bound triphenylphosphine (˜3 mmol/g, 0.628 g, 1.885 mmol) and the reaction mixture stirred at room temperature for 4 days. 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 0.5 to 5% ammonia saturated methanol solution in dichloromethane gave 159 mg (82%) of {[(2R)-8-(2,6-dichlorophenyl)-3,4-dihydro-2H-chromen-2-yl]methyl}amine as a colorless syrup. The product was dissolved in 2-propanol (1 mL) and diethyl ether (2.5 mL) and a solution of hydrogen chloride (1.0 M in diethyl ether, 0.517 mL, 0.517 mmol) was added followed by hexane (2 mL). The resulting white precipitate was filtered to afford 155 mg (72%) of {[(2R)-8-(2,6-dichlorophenyl)-3,4-dihydro-2H-chromen-2-yl]methyl}amine hydrochloride as a white crystalline solid, mp 188–190° C.; [α]D25=−6.74° (c=5.4 mg/0.7 mL 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 reduced pressure
  4. customto afford a yellow syrup
  5. customPurification by flash chromatography

Sources & evidence

ORD record
ord-459e25dfd54043dda6494f39f1801339
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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