Ethylamine → N,N-Diisopropyl-3-(5-ethylaminomethyl-2-hydroxyphenyl)-3-phenylpropanamine

HRID 428329ノート

反応式

HRID 428329 の反応式
[CH:1]([N:4]([CH:23]([CH3:25])[CH3:24])[CH2:5][CH2:6][C@@H:7]([C:14]1[CH:19]=[C:18]([CH:20]=O)[CH:17]=[CH:16][C:15]=1[OH:22])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:3])[CH3:2].[CH2:26]([NH2:28])[CH3:27].C([BH3-])#N.[Na+]>CO>[CH:23]([N:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][CH2:6][CH:7]([C:14]1[CH:19]=[C:18]([CH2:20][NH:28][CH2:26][CH3:27])[CH:17]=[CH:16][C:15]=1[OH:22])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([CH3:25])[CH3:24]

参加物

5

反応物 3

HCID 6341EthylamineHCID 5003444Sodium cyanoborohydrideHCID 53380832(R)-N,N-diisopropyl-3-(5-formyl-2-hydroxyphenyl)-3-phenylpropanamine

生成物 1

HCID 18357409N,N-Diisopropyl-3-(5-ethylaminomethyl-2-hydroxyphenyl)-3-phenylpropanamine

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

(R)-N,N-Diisopropyl-3-(5-formyl-2-hydroxyphenyl)-3-phenylpropanamine (prepared in Example 7.1) (1.23 g, 3.62 mmol) was dissolved in methanol (20 mL). Ethylamine [3.62 mL, 21.7 mmol (6M hydrochloric acid in methanol)] and sodium cyanoborohydride (0.14 g, 2.17 mmol) were added. The mixture was stirred overnight at room temperature. The solvent was evaporated and the residue was chromatographed on silica (toluene-ethyl acetate-triethylamine 7:3:1). The product was dissolved in diethyl ether and hydrogen chloride in diethyl ether was added. The resulting oil was stirred in diethyl ether over night to give crystals. Yield 0.70 g (44%); mp. 140-142° C.; [α]D−5.0° (c=0.5, methanol); 1H NMR (CD3OD) δ1.30 (m, 15H), 2.59 (m, 2H), 3.05 (m, 4H), 3.70 (m, 2H), 4.07 (s, 2H), 4.42 (t, 1H), 6.85 (d, 1H), 7.20 (m, 2H), 7.30 (t, 2H), 7.41 (d, 2H), 7.50 (s, 1H) Anal. (C24H36N2O*2.0 HCl*0.5H2O) C,H,N.

後処理

  1. customThe solvent was evaporated
  2. customthe residue was chromatographed on silica (toluene-ethyl acetate-triethylamine 7:3:1)
  3. dissolutionThe product was dissolved in diethyl ether
  4. additionhydrogen chloride in diethyl ether was added
  5. stirringThe resulting oil was stirred in diethyl ether over night
  6. customto give crystals

出典と根拠

ORDレコード
ord-5be98d07de0146a09fac8eb164d3e77b
出典データセット
uspto-grants-2001_11
特許番号
US06313132B1

反応ノート

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