Aluminium lithium hydride → 1-(diphenylmethyl)-3-{[(1-methylethyl)amino]methyl}-N-(phenylmethyl)azetidin-3-amine

HRID 1672916노트

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HRID 1672916 반응식
[C:1]1([CH:7]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:8]2[CH2:11][C:10]([NH:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)([C:12]([NH:14][CH:15]([CH3:17])[CH3:16])=O)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[C:26]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:11][C:10]([CH2:12][NH:14][CH:15]([CH3:17])[CH3:16])([NH:18][CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:9]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 670518131-(diphenylmethyl)-N-(1-methylethyl)-3-[(phenylmethyl)amino]azetidine-3-carboxamide

생성물 1

HCID 670515751-(diphenylmethyl)-3-{[(1-methylethyl)amino]methyl}-N-(phenylmethyl)azetidin-3-amine수율 90.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
50 °C

실험 절차

To a solution of the 1-(diphenylmethyl)-N-(1-methylethyl)-3-[(phenylmethyl)amino]azetidine-3-carboxamide (0.40 g, 0.97 mmol) in tetrahydrofuran (10 mL) at room was added a solution of lithium aluminum hydride in tetrahydrofuran (1M, 2.90 mL, 2.90 mmol), and the resulting mixture was stirred at 50° C. for 3 h. The reaction mixture was cooled to room temperature, quenched with 20% aqueous hydroxide solution (1 mL), diluted with ether (50 mL) and filtered. The filtrate was washed with brine solution (20 mL each), dried over sodium sulfate, filtered and concentrated to give an oily residue which was purified by flash chromatography (silica gel, eluting with 5% methanol-dichloromethane) to give 1-(diphenylmethyl)-3-{[(1-methylethyl)amino]methyl}-N-(phenylmethyl)azetidin-3-amine (0.35 g, 90% yield), 1H NMR (400 MHz, CDCl3): 7.42-7.14 (m, 15H), 4.34 (s, 1H), 3.66 (s, 2H), 3.22-3.18 (d, 2H), 2.97 (s, 2H), 2.90-2.86 (d, 2H), 2.68-2.62 (p, 1H), 1.09-1.07 (d, 6H); MS (EI) for C27H33N3: 400 (MH+).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customquenched with 20% aqueous hydroxide solution (1 mL)
  3. additiondiluted with ether (50 mL)
  4. filtrationfiltered
  5. washThe filtrate was washed with brine solution (20 mL each)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give an oily residue which
  10. customwas purified by flash chromatography (silica gel, eluting with 5% methanol-dichloromethane)

출처 및 근거

ORD 기록
ord-9357a88645854917ae86dc2d1e2e3e45
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07999006B2

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