Red-Al → 1-phenyl-N-{[(3S)-4-(phenylmethyl)-3-morpholinyl]methyl}methanamine

HRID 419386노트

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HRID 419386 반응식
O=[C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C@@H:6]([C:15]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=O)[CH2:5][O:4][CH2:3]1.COCCO[AlH2-]OCCOC.[Na+]>C1(C)C=CC=CC=1>[C:19]1([CH2:18][NH:17][CH2:15][C@H:6]2[CH2:5][O:4][CH2:3][CH2:2][N:7]2[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

참가 물질

4

반응물 2

HCID 16684438Red-AlHCID 59452664(3R)-5-oxo-N,4-bis(phenylmethyl)-3-morpholinecarboxamide

생성물 1

HCID 594527491-phenyl-N-{[(3S)-4-(phenylmethyl)-3-morpholinyl]methyl}methanamine수율 94.2%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
50 °C

실험 절차

(3R)-5-oxo-N,4-bis(phenylmethyl)-3-morpholinecarboxamide (5.09 g, 15.6 mmol) in toluene (50 mL) cooled to 0° C. Red-Al® (35.0 mL, 7 mL per g carboxamide) added via addition funnel. The ice bath was removed after 2 or 3 mL Red-Al® was added. The reaction was heated at 50° C. overnight. The reaction was cooled to 0° C. and quenched slowly with 1N NaOH (50 mL) followed by diethyl ether (50 mL). The organic layer was washed with 1N NaOH (50 mL), the combined aqueous layer was back extracted with toluene (50 mL) and diethyl ether (50 mL) and dried over MgSO4 to provide the title compound of step D (4.35 g, 14.7 mmol, 94%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.97 (br. s., 1H), 2.06 (ddd, J=12.0, 9.2, 3.4 Hz, 1H), 2.33-2.41 (m, 1H), 2.43-2.48 (m, 1H), 2.54-2.66 (m, 2H), 3.13 (d, J=13.6 Hz, 1H), 3.32-3.39 (m, 1H), 3.42 (dd, J=11.2, 8.2 Hz, 1H), 3.53 (dt, J=11.1, 3.5 Hz, 1H), 3.57-3.62 (m, 2H), 3.70 (dd, J=11.1, 3.0 Hz, 1H), 3.93 (d, J=13.6 Hz, 1H), 7.16-7.27 (m, 10H).

후처리

  1. customThe ice bath was removed after 2 or 3 mL Red-Al®
  2. additionwas added
  3. temperatureThe reaction was cooled to 0° C.
  4. customquenched slowly with 1N NaOH (50 mL)
  5. washThe organic layer was washed with 1N NaOH (50 mL)
  6. extractionthe combined aqueous layer was back extracted with toluene (50 mL) and diethyl ether (50 mL)
  7. dry with materialdried over MgSO4

출처 및 근거

ORD 기록
ord-d24251f530e24db4bd5cdb6105ade199
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093239B2

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