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

HRID 556162ノート

反応式

HRID 556162 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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

後処理

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

出典と根拠

ORDレコード
ord-aa5b9c53fdbc40308867581d89b4445f
出典データセット
uspto-grants-2011_11
特許番号
US08053603B2

反応ノート

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