Methanol → HCID 15942620, compound

HRID 902335Notes

Reaction equation

HRID 902335 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[Cl:22])[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-]>[Cl: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 86609123HCID 86609123, compound

Product 1

HCID 15942620HCID 15942620, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 14923Ammonium HydroxideSolvent

Procedure

To a solution of (R)-2-azidomethyl-8-(2-chloro-phenyl)-6-fluoro-chroman (210 mg, 0.67 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-chlorophenyl)-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 (56 mg, 25%) as a beige solid using excess ethereal hydrochloric acid, mp 145–147° C.; [α]D25=+256.01° (c=5.3 mg/0.7 mL MeOH).

Workup

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

Sources & evidence

ORD record
ord-6dba26affedf4d5abbd0487e5acd6687
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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