Methanol → [(R)-6-fluoro-8-(2-methoxyphenyl)-3,4-dihydro-2H-chromen-2-yl]methanamine

HRID 902318

반응식

HRID 902318 반응식
[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(C(Cl)Cl)C.[NH4+].[OH-]>[F:15][C:10]1[CH:11]=[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]=1)[O:6][C@@H:5]([CH2:4][NH2:1])[CH2:14][CH2:13]2

참가 물질

8

반응물 3

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

생성물 1

HCID 15942471[(R)-6-fluoro-8-(2-methoxyphenyl)-3,4-dihydro-2H-chromen-2-yl]methanamine

시약·촉매·용매 4

HCID 962Water용매HCID 65731,1-Dichloropropane용매HCID 8028Tetrahydrofuran용매HCID 14923Ammonium Hydroxide용매

실험 절차

To a solution of (R)-2-(azidomethyl)-6-fluoro-8-(2-methoxyphenyl)-chroman (210 mg, 0.67 mmol) in tetrahydrofuran (15 mL) and water (0.5 mL) was added triphenylphosphine (0.21 g, 0.80 mmol) and the reaction mixture stirred at room temperature for 24 hours. Chromatography with 0–10% methanol in ethyl methylene chloride plus 1% NH4OH afforded [(R)-6-fluoro-8-(2-methoxyphenyl)-3,4-dihydro-2H-chromen-2-yl]methanamine as a colorless oil. The oil was dissolved in ethyl acetate and made into its hydrochloride salt (0.95 g, 69%) as a white solid using excess ethereal hydrochloric acid, mp 100° C. decomposed; MS (ES) m/z 288.1 ([M+H]+); [α]D25=−34.64° (c=5.7 mg/0.7 mL MeOH).

출처 및 근거

ORD 기록
ord-8e5b20030d6648e7a7c80d65b2bf6a29
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07365095B2

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