Potassium tert-butoxide → (S)-3-methoxymethylamino-1-(2-thienyl)propan-1-ol

HRID 1915185ノート

反応式

HRID 1915185 の反応式
[CH3:1][O:2][CH2:3][NH:4][CH2:5][CH2:6][C:7]([C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)=[O:8].CC(C)([O-])C.[K+].[H][H]>CO>[CH3:1][O:2][CH2:3][NH:4][CH2:5][CH2:6][C@@H:7]([C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)[OH:8]

参加物

5

反応物 3

HCID 23665647Potassium tert-butoxideHCID 66769536HCID 66769536、化合物HCID 178418361HCID 178418361、化合物

生成物 1

HCID 66769498(S)-3-methoxymethylamino-1-(2-thienyl)propan-1-ol

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

4 mL of degassed methanol solution containing 10 mg of RuCl2((R)-3,5-xylylBINAP) ((2R)-DAIPEN), 160 mg of 3-methoxymethylamino-1-(2-thienyl)-1-propanone, 100 mg of potassium tert-butoxide and 10 mL of methanol were charged in a glass autoclave under an argon gas flow. After deaeration and replacement by argon, hydrogen was introduced to a predetermined pressure. The resulting solution was hydrogenated at 20□ for 12 hours. Upon completion of hydrogenation, the reaction mixture was concentrated, and then the desired compound is obtained as an oily product (161 mg, 95.8% by HPLC assay, 95% ee). 1H NMR (400 MHz, CDCl3) δ (ppm)=3.0 (s, 3H), 3.0-3.1 (m, 1H), 4.1 (s, 3H), 4.0-4.1 (m, 3H), 6.1 (dt, J=7.4, 15.4 Hz, 1H), 6.9 (d, J=15.7 Hz, 1H), 7.0 (dd, J=3.7, 5.0 Hz, 1H), 7.1 (d, J=3.4 Hz, 1H).

後処理

  1. additionwere charged in a glass autoclave under an argon gas flow
  2. concentrationUpon completion of hydrogenation, the reaction mixture was concentrated

出典と根拠

ORDレコード
ord-125b1ddb6f1544d684b53f59d2768480
出典データセット
uspto-grants-2013_12
特許番号
US08614336B2

反応ノート

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