Methanol → {[(R)-8-(2-methoxyphenyl)-6-fluoro-2H-chromen-2-yl]methyl}amine

HRID 902337Notes

Reaction equation

HRID 902337 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[O:22][CH3:23])[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>O1CCCC1.O.C(Cl)Cl.[NH4+].[OH-]>[CH3:23][O:22][C:17]1[CH:18]=[CH:19][CH:20]=[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

8

Reactant 3

HCID 887MethanolHCID 11776TriphenylphosphineHCID 86609113(R)-2-azidomethyl-8-(2-methoxyphenyl)-6-fluoro-chroman

Product 1

HCID 59701548{[(R)-8-(2-methoxyphenyl)-6-fluoro-2H-chromen-2-yl]methyl}amine

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 14923Ammonium HydroxideSolvent

Procedure

To a solution of (R)-2-azidomethyl-8-(2-methoxyphenyl)-6-fluoro-chroman (190 mg, 0.32 mmol) in tetrahydrofuran (10 mL) and water (0.5 mL) was added triphenylphosphine (0.26 g, 10 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-methoxyphenyl)-6-fluoro-2H-chromen-2-yl]methyl}amine as a colorless oil. The colorless oil was dissolved in ethyl acetate and made into its hydrochloride salt (119 mg, 61%) as an off-white crystalline solid, mp 198–200° C.; [α]D25=+173.89° (c=5.2 mg/0.7mL MeOH).

Workup

  1. customThe solvent was removed under vacuum
  2. customto form a colorless oil

Sources & evidence

ORD record
ord-df21f2ee12534b0d992aa75e82bebba5
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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