Hydrochloric Acid → HCID 69117520, compound

HRID 902333Notes

Reaction equation

HRID 902333 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]=[C:20]([Cl:22])[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.CO.Cl>O1CCCC1.O.C(Cl)Cl.[NH4+].[OH-].C(OCC)(=O)C>[ClH:22].[Cl:23][C:17]1[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][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

10

Reactant 4

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 11776TriphenylphosphineHCID 86609122HCID 86609122, compound

Product 1

HCID 69117520HCID 69117520, compound

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 14923Ammonium HydroxideSolvent

Procedure

To a solution of (R)-2-azidomethyl-8-(2,5-dichloro-phenyl)-6-fluoro-chroman (240 mg, 0.68 mmol) in tetrahydrofuran (10 mL) and water (0.5 mL) was added triphenylphosphine (0.27 g, 10.2 mmol) and the reaction mixture stirred at room temperature for 24 hours. The solvent was removed under vacuum to form a colorless oil. Chromatography with 0–5% methanol in methylene chloride plus 1% NH4OH afforded {[(R-8-(2.5-dichlorophenyl)-6-fluoro-2H-chromen-2-yl]methyl}amine as a colorless oil. The oil was dissolved in ethyl acetate and made into its hydrochloride salt (121 mg, 45%) using excess ethereal hydrochloric acid to give a white solid, mp 217–219° C.; MS (ES) m/z 324.0 ([M+H]+); [α]D25=+191.22° (c=5.1 mg/0.7 mL MeOH).

Workup

  1. customThe solvent was removed under vacuum
  2. customto form a colorless oil
  3. customto give a white solid, mp 217–219° C.

Sources & evidence

ORD record
ord-c1b4b8f1597c43d983b135c2b7023e69
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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