1-Naphthaldehyde → 1-{(S)-[methyl-((S)-1-phenyl-ethyl)-amino]-naphthalen-1-yl-methyl}-naphthalen-2-ol

HRID 735395

반응식

HRID 735395 반응식
[C:1]1([CH:11]=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH3:13][NH:14][C@@H:15]([CH3:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[CH:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][C:24]=1[OH:33]>CO>[CH3:13][N:14]([C@@H:11]([C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1)[C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][C:24]=1[OH:33])[C@H:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:22]

참가 물질

5

반응물 3

HCID 61951-NaphthaldehydeHCID 86632-NaphtholHCID 2060073(S)-(-)-N,alpha-Dimethylbenzylamine

생성물 1

HCID 112238231-{(S)-[methyl-((S)-1-phenyl-ethyl)-amino]-naphthalen-1-yl-methyl}-naphthalen-2-ol수율 51%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
85 °C

실험 절차

1-Naphthaldehyde (2.7 mL, 20 mmol), (S)-(−)-N,α-dimetylbenzylamine (2.60 g, 19 mmol) and 2-naphthol (2.43 g, 16 mmol) are charged into a 25 mL flask with a magnetic stirring bar. The mixture is heated to 85° C. and stirred for 72 h. After the system is cooled to RT, MeOH (5 mL) is added and the precipitated product is collected by filtration, washed with MeOH (5 mL) and dried to afford 1-{(S)-[methyl-((S)-1-phenyl-ethyl)-amino]-naphthalen-1-yl-methyl}-naphthalen-2-ol as white crystals (about 51% yield): 1H NMR (500 MHz, CDCl3) δ 14.01 (br s, 1H), 7.77-7.02 (m, 18H), 6.45 (s, 1H), 4.40 (br s, 1H), 1.95 (s, 3H), 1.65 (br s, 3H); MS (EI) m/z (rel intensity) 418 (M++1), 283, 141, 136; HRMS (EI) Calcd for C30H28NO (M++1): 418.2171, found 418.2135.

후처리

  1. temperatureAfter the system is cooled to RT
  2. filtrationthe precipitated product is collected by filtration
  3. washwashed with MeOH (5 mL)
  4. customdried

출처 및 근거

ORD 기록
ord-2f55e3e8972c41f694b8b10764232ea7
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592487B2

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