Triphenylphosphine → HCID 69117208, compound

HRID 902352Notes

Reaction equation

HRID 902352 reaction equation
[N:1]([CH2:4][C@H:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH3:22])[C:9]([Cl:15])=[CH:10][CH:11]=2)[O:6]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[ClH:15].[Cl:15][C:9]1[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])=[C:7]2[C:12]([CH2:13][CH2:14][C@H:5]([CH2:4][NH2:1])[O:6]2)=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 86609135HCID 86609135, compound

Product 1

HCID 69117208HCID 69117208, compoundYield 57.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2R)-2-(azidomethyl)-7-chloro-8-o-tolylchroman (0.5 g, 1.6 mmol) in THF (15 mL) and water (0.5 mL) was added polymer-bound triphenylphosphine (3 mmol/g, 0.8 g, 2.4 mmol) and the resulting mixture was stirred at room temperature overnight. The mixture was filtered through a pad of Celite and concentrated under reduced pressure. Purification by ISCO using a solvent gradient of 0 to 10% methanol in methylene chloride provided 0.15 g of the title compound as a colorless oil. The oil was dissolved in ethyl acetate (5 mL) and to which hydrogen chloride (1.0 M in ethyl ether, 1.5 mL, 1.5 mmol) was added, solvent was removed and the solid was washed with ethyl ether (3×5 mL) to provide 0.13 g of ((2R)-7-chloro-8-o-tolylchroman-2-yl)methanamine hydrochloride as a white solid salt, mp 155° C.; MS (APPI) m/z 288 ([M+H]+); [α]D25=−55° (c=1% SOLN, MeOH).

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. concentrationconcentrated under reduced pressure
  3. customPurification by ISCO

Sources & evidence

ORD record
ord-a06d395c0fa243d88feef7f80101335d
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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