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

HRID 735395

反応式

HRID 735395 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
85 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-2f55e3e8972c41f694b8b10764232ea7
出典データセット
uspto-grants-2009_09
特許番号
US07592487B2

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