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

HRID 14419

반응식

HRID 14419 반응식
[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

참가 물질

3

반응물 2

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

생성물 1

HCID 10082333N-benzyl-1-phenyl-2-propen-1-amine수율 80%

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-44b0229e1d05449799b74d31c084fb29
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732365B2

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