3-Quinuclidinol, (-)- → (R)-3-(4-phenoxyphenoxy)quinuclidine

HRID 1294644

반응식

HRID 1294644 반응식
[OH:1][C@@H:2]1[CH:7]2[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]2)[CH2:3]1.I[C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:13][CH:12]=1>>[O:17]([C:18]1[CH:19]=[CH:20][C:21]([O:1][C@@H:2]2[CH:7]3[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]3)[CH2:3]2)=[CH:22][CH:23]=1)[C:14]1[CH:15]=[CH:16][CH:11]=[CH:12][CH:13]=1

참가 물질

3

반응물 2

HCID 914043-Quinuclidinol, (-)-HCID 5203994-Iododiphenyl ether

생성물 1

HCID 11449311(R)-3-(4-phenoxyphenoxy)quinuclidine

실험 절차

3-(R)-Hydroxy-quinuclidine (the product of Reference Example 1, 152 mg, 1.2 mmol), was coupled with 1-iodo-4-phenoxy-benzene (178 mg, 0.6 mmol) according to the procedure of Example 3A. The title product was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.20) as oil (25 mg, yield, 14%). 1H NMR (MeOH-d4, 300 MHz) δ 1.45–1.58 (m, 1H), 1.64–1.85 (m, 2H), 2.00–2.15 (m, 1H), 2.20–2.30 (m, 1H), 2.70–3.10 (m, 5H), 3.34–3.40 (m, 1H), 4.52 (m, 1H), 6.83–6.98 (m, 6H), 7.03 (tt, J=7.5, 1.0 Hz, 1H), 7.30 (t, J=7.5 Hz, 2H) ppm. MS (DC m/z 296 (M+H)+.

후처리

  1. customThe title product was purified by chromatography (SiO2, CH2Cl2:MeOH:NH3.H2O, 90:10:1, Rf. 0.20) as oil (25 mg, yield, 14%)

출처 및 근거

ORD 기록
ord-4727975dec6f4b3388c26e9e947c290e
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07241773B2

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