Methanol → (S)-(+)-N-methyl-3-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine

HRID 1686175ノート

反応式

HRID 1686175 の反応式
[CH3:1][N:2]([CH2:5][CH2:6][CH:7]([O:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)[C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)OC.[CH3:24]O>[Ni]>[CH3:1][NH:2][CH2:5][CH2:6][C@:7]([CH3:24])([O:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)[C:8]1[S:9][CH:10]=[CH:11][CH:12]=1

参加物

4

反応物 2

HCID 887MethanolHCID 46913234N-methyl-N-methoxyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine

生成物 1

HCID 42598152(S)-(+)-N-methyl-3-methyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine

試薬・触媒・溶媒 1

HCID 935Nickel触媒

実験手順

N-methyl-N-methoxyl-3-(1-naphthyloxy)-3-(2-thienyl)propylamine obtained in example 3 was dissolved in 15 mL of methanol with 0.67 g of Raney-nickel were charged in a glass autoclave. The resulting solution was hydrogenated at 50□ for 12 hours. Upon completion of hydrogenation the reaction mixture was filtered and solvent is removed under reduced pressure, and then the desired compound is obtained as an oily compound (12.0 g, 96.4% by HPLC assay). 1H NMR (400 MHz, CDCl3) δ (ppm)=2.2 (m, 1H), 2.4 (m, 1H), 2.4 (s, 3H), 2.8 (m, 2H), 5.8 (m, 1H), 6.8 (d, 1H), 6.9 (m, 1H), 7.1 (d, 1H), 7.2 (d, 1H), 7.3 (d, 1H), 7.4 (m, 1H), 7.5 (m, 2H), 7.8 (m, 1H), 8.3 (m, 1H).

後処理

  1. additionwere charged in a glass autoclave
  2. filtrationUpon completion of hydrogenation the reaction mixture was filtered
  3. customsolvent is removed under reduced pressure

出典と根拠

ORDレコード
ord-6a9e6e6fee484852bec3064b5b6db641
出典データセット
uspto-grants-2012_04
特許番号
US08148549B2

反応ノート

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