Ethanone, 1-phenyl-, dihydroxy deriv. → N-(2-phenyl-2-hydroxyethyl)-4-(N-Boc-2-aminoethyl)aniline

HRID 1349399ノート

反応式

HRID 1349399 の反応式
[C:1]([NH:8][CH2:9][CH2:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O[CH:19](O)[C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:21].[BH3-]C#N.[Na+]>CO>[C:22]1([CH:20]([OH:21])[CH2:19][NH:15][C:14]2[CH:16]=[CH:17][C:11]([CH2:10][CH2:9][NH:8][C:1]([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2])=[CH:12][CH:13]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

5

反応物 3

HCID 99611Ethanone, 1-phenyl-, dihydroxy deriv.HCID 382207Tert-butyl 4-aminophenethylcarbamateHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 21959862N-(2-phenyl-2-hydroxyethyl)-4-(N-Boc-2-aminoethyl)aniline収率 91%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

4-(N-Boc-2-aminoethyl)aniline 28 (1.25 g, 5.29 mmole) was dissolved in methanol (30 mL), followed by addition of phenyl glyoxal 24 (0.708 g, 5.28 mmole). The reaction mixture was stirred for 1 h at rt, prior to addition of NaCNBH3 (0.665 g, 10.6 mmole). The final mixture was stirred for 12 h at rt, concentrated, and purified by flash silica column chromatography (2 to 5% MeOH/CH2Cl2) to give N-(2-phenyl-2-hydroxyethyl)-4-(N-Boc-2-aminoethyl)-aniline as a pale yellow oil (1.71 g, 91%): Rf=0.18 in 5% MeOH/CH2Cl2. 1H-NMR (CD3OD, 299.96 MHz): δ (ppm) 7.4–7.25 (m, 5H), 7.0–6.95 (d, 2H), 6.63–6.60 (d, 2H), 4.85–4.79 (dd, 1H), 3.3–3.21 (t, 2H),3.2–3.15 (m, 2H), 2.64–2.5 (t, 2H), 1.42 (s, 9H).

後処理

  1. concentrationconcentrated
  2. custompurified by flash silica column chromatography (2 to 5% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-d63c03fab6e74a72ad02d7e59b618e4f
出典データセット
uspto-grants-2007_05
特許番号
US07211695B2

反応ノート

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