Formic Acid → 1-((S)-4-(3,4-dichlorophenyl)-3,4-dihydronaphthalen-2-yl)-N,N-dimethylethanamine

HRID 556162노트

반응식

HRID 556162 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]([CH:19]([NH:21][CH3:22])[CH3:20])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].C=O.[CH:25](O)=O>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]([CH:19]([N:21]([CH3:25])[CH3:22])[CH3:20])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

참가 물질

5

반응물 3

HCID 284Formic AcidHCID 712FormaldehydeHCID 589507521-((S)-4-(3,4-dichlorophenyl)-3,4-dihydronaphthalen-2-yl)-N-methylethanamine

생성물 1

HCID 589507491-((S)-4-(3,4-dichlorophenyl)-3,4-dihydronaphthalen-2-yl)-N,N-dimethylethanamine수율 91%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 47 (200 mg, 0.60 mmol) in MeOH (5 mL) was added HCHO (35 mg, 37%, 1.20 mml), HCO2H (0.3 mL) and NaB(CN)H3 (75 mg, 1.20 mmol). The reaction mixture was stirred for 20 min before being concentrated. The residue was dissolved in MeOH (2 mL) and subjected to reverse phase column chromatography (CH3CN/H2O/0.1% formic acid=5% to 100%) to give 48 (188 mg, 91%). 1H NMR (400 MHz, CDCl3)δ 7.34 (d, J=8.4 Hz, 1 H), 7.25 (m, 2 H), 7.20 (m, 2 H) 7.12 (m, 2 H), 7.0 (dd, J=2.0, 8.4 Hz, 1 H), 6.83 (d, J=7.6Hz, 1 H), 6.40 (s, 1 H), 4.10 (t, J=8.4 Hz, 1 H), 2.65 (d, t, J=6.4, 13.2 Hz, 1 H), 2.65 (dd, J=6.8, 16.4 Hz, 1 H), 2.54 (dd, J=9.2, 16.4 Hz, 1 H), 2.21 (s, 6 H), 1.01 (d, J=6.8 Hz, 1 H); 13C NMR (100 m Hz, CDCl3)δ 144.87, 142.04, 136.44, 134.67, 132.42, 130.61, 130.45, 128.16, 127.78, 127.53, 177.43, 126.61, 124.19, 124.12, 67.03, 43.72, 43.83, 43.50, 32.36, 16.45; ESI MS m/z 346.1

후처리

  1. concentrationbefore being concentrated
  2. dissolutionThe residue was dissolved in MeOH (2 mL)

출처 및 근거

ORD 기록
ord-aa5b9c53fdbc40308867581d89b4445f
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08053603B2

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