Triphenylphosphine → 6-[(4-Fluoro-3-methylphenoxy)methyl]-1-benzyl-2-methylazepane

HRID 467479ノート

反応式

HRID 467479 の反応式
[CH2:1]([N:8]1[CH:14]([CH3:15])[CH2:13][CH2:12][CH2:11][CH:10]([CH2:16][OH:17])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:18][C:19]1[CH:24]=[CH:23][C:22](O)=[CH:21][C:20]=1[CH3:26].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>ClCCl>[F:18][C:19]1[CH:24]=[CH:23][C:22]([O:17][CH2:16][CH:10]2[CH2:9][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:14]([CH3:15])[CH2:13][CH2:12][CH2:11]2)=[CH:21][C:20]=1[CH3:26]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 27373944-Fluoro-3-methylphenolHCID 5363146Diisopropyl azodicarboxylateHCID 58405271HCID 58405271、化合物

生成物 1

HCID 584052656-[(4-Fluoro-3-methylphenoxy)methyl]-1-benzyl-2-methylazepane

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
23 °C

実験手順

A mixture of (1-benzyl-7-methylazepan-3-yl)methanol (2-5, 500 mg, 2.1 mmol, 1.0 equiv), 4-fluoro-3-methylphenol (300 mg, 2.4 mmol, 1.1 equiv), and PS-triphenyl phosphine resin (1.2 g, 2.4 mmol, 1.1 equiv) in dichloromethane (25 mL) was treated with DIAD (0.46 mL, 480 mg, 2.4 mmol, 1.1 equiv) and the resulting suspension was stirred for 16 hours at 23° C. The mixture was filtered and filtrate was concentrated. The residue was purified by silica gel chromatography (0-100% ethyl acetate/hexanes gradient) to yield 6-[(4-fluoro-3-methylphenoxy)methyl]-1-benzyl-2-methylazepane (2-6) as a clear oil. 1H NMR (400 MHz, CDCl3) δ 7.37 (m, 5H), 6.86 (m, 1H), 6.55 (m, 2H), 3.72-1.75 (m, 20H). LRMS m/z (M+H) 342.3 found, 242.2 required.

後処理

  1. filtrationThe mixture was filtered
  2. concentrationfiltrate was concentrated
  3. customThe residue was purified by silica gel chromatography (0-100% ethyl acetate/hexanes gradient)

出典と根拠

ORDレコード
ord-32c01b6a9d714b4991b1ec293b00f8f0
出典データセット
uspto-grants-2014_01
特許番号
US08623863B2

反応ノート

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