4-Methoxybenzylamine → N-benzyl-1-phenyl-2-propen-1-amine

HRID 14419

反応式

HRID 14419 の反応式
[C:1]1([CH:7]([NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15](OC)=[CH:14][CH:13]=2)[CH:8]=[CH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.COC1C=CC(CN)=CC=1>>[C:1]1([CH:7]([NH:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:8]=[CH2:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

3

反応物 2

HCID 754524-MethoxybenzylamineHCID 11615799n-(1-Phenyl-2-propenyl)-4-methoxybenzylamine

生成物 1

HCID 10082333N-benzyl-1-phenyl-2-propen-1-amine収率 80%

実験手順

N-(1-Phenyl-2-propenyl)-4-methoxybenzylamine (Yadav, J. S.; Bandyopadhyay, A.; Reddy, B. V. S. Tetrahedron Lett. 2001, 42, 6385: The general procedure was followed with 4-methoxybenzylamine (186 mg, 1.35 mmol) and cinnamyl methylcarbonate (199 mg, 1.04 mmol). The reaction was conducted at room temperature for 18 h. 1H NMR analysis of the crude mixture indicated the ratio of regioisomers and diallylation product to be 98/0/2. The mixture was purified by flash column chromatography on silica gel (5% ethyl acetate in hexane) to give the title compound (210 mg, 80%). HPLC analysis indicated that the enantiomeric excess of product was 94% [Daicel CHIRALCEL OD-H (0.46 cm×25 cm); hexane/2-propanol=99.75/0.25; flow rate=0.5 mL/min; detection wave length=230 nm; TR=26.2 (major), 29.3 (minor) min]: [α]DRT=−1.8 (c 5.5, CHCl3). 1H NMR (400.13 MHz, CDCl3) δ 7.21-7.38 (m, 7H), 6.86 (d, J=8.4 Hz, 2H), 5.94 (ddd, J=17.2, 10.0, 7.6 Hz, 1H), 5.22 (dt, J=17.2, 1.4 Hz, 1H), 5.11 (ddd, J=10.0, 1.6, 1.2 Hz, 1H), 4.21 (d, J=7.6 Hz, 1H), 3.80 (s, 3H), 3.68 (d of AB pattern, J=13.0 Hz, 1H), 3.64 (d of AB pattern, J=13.0 Hz, 1H), 1.58 (brs, 1H). 13C NMR (125.77 MHz, CDCl3) δ 158.54, 142.84, 141.01, 132.56, 129.29, 128.49, 127.30, 127.14, 115.05, 113.72, 64.99, 55.24, 50.65.

後処理

  1. customThe mixture was purified by flash column chromatography on silica gel (5% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-44b0229e1d05449799b74d31c084fb29
出典データセット
uspto-grants-2010_06
特許番号
US07732365B2

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