HCID 67315923, 화합물 → Ethyl β-methyl-2-naphthalenepropanoate

HRID 1014766노트

반응식

HRID 1014766 반응식
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([CH3:18])=[CH:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]>[Ir].C(Cl)Cl>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]([CH3:18])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]

참가 물질

4

반응물 1

HCID 67315923HCID 67315923, 화합물

생성물 1

HCID 57055028Ethyl β-methyl-2-naphthalenepropanoate수율 99%

시약·촉매·용매 2

HCID 23924Iridium촉매HCID 6344Dichloromethane용매

실험 절차

According to the general procedure, a solution of ethyl 3-(naphthalen-2-yl)-but-2-enoate) (70 mg, 0.29 mmol) and iridium catalyst (S)-32 (9.2 mg, 0.0058 mmol, 2.0 mol %) in CH2Cl2 (3 mL) was hydrogenated. Removal of the solvent in vacuo and standard purification gave 38 (70 mg, 99%) as a colorless oil. [α]20D −25.9 (c 1.02, CHCl3); CSP HPLC analysis (Chiralcel OD-H; eluent: 99.5:0.5 hexanes/i-PrOH, 1.0 ml/min) determined a 89.5:10.5 er (79% ee) [tR(minor) 12.34 min, tR(major) 14.19 min]; 1H NMR (300 MHz, CDCl3) 7.82 (d, 3H, J=8.4 Hz), 7.69 (s, 1H), 7.51-7.39 (m, 3H), 4.11 (q, 2H, J=7.2 Hz), 3.50 (sextet, 1H, J=7.5 Hz), 2.81-2.62 (m, 2H), 1.42 (d, 3H, J=6.9 Hz), 1.19 (t, 3H, J=7.2 Hz) ppm; 13C NMR (75 MHz, CDCl3) 172.3, 143.1, 135.5, 132.3, 128.1, 127.6, 127.5, 125.9, 125.4, 125.3, 124.9, 60.2, 42.8, 42.6, 36.6, 21.7, 14.1 ppm.

후처리

  1. customRemoval of the solvent
  2. customin vacuo and standard purification

출처 및 근거

ORD 기록
ord-534bff48ce4742908e4a2ad9a75fa60d
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07982064B2

반응 노트

불러오는 중…