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

HRID 428329노트

반응식

HRID 428329 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-5be98d07de0146a09fac8eb164d3e77b
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313132B1

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