Gramine → (2,3-dihydro-1H-indol-3-ylmethyl)dimethylamine

HRID 880178

反応式

HRID 880178 の反応式
C([BH3-])#N.[Na+].[CH3:5][N:6]([CH2:8][C:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[NH:11][CH:10]=1)[CH3:7]>FC(F)(F)C(O)=O>[NH:11]1[C:12]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:9]([CH2:8][N:6]([CH3:7])[CH3:5])[CH2:10]1

参加物

4

反応物 2

HCID 6890GramineHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 13156058(2,3-dihydro-1H-indol-3-ylmethyl)dimethylamine収率 65.2%

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

反応条件

温度
0 °C

実験手順

1.1 g of sodium cyanoborohydride is gradually added to a solution of 1 g of gramine in 20 ml of trifluoroacetic acid, under argon, cooled in an ice bath, and stirred for half an hour at 0° C. and then for 2 h at ambient temperature. The reaction medium is plunged into 50 g of ice and alkalinized using 30% sodium hydroxide, and is then extracted with four times 30 ml of ethyl acetate. The organic phase is washed with 20 ml of water, dried over anhydrous magnesium sulphate, filtered, and then concentrated to dryness under reduced pressure. After a silica column purification, eluent: 85/15 v/v CH2Cl2/MeOH, 660 mg of (2,3-dihydro-1H-indol-3-ylmethyl)dimethylamine are obtained in the form of a yellow solid, the characteristics of which are the following:

後処理

  1. temperaturecooled in an ice bath
  2. extractionalkalinized using 30% sodium hydroxide, and is then extracted with four times 30 ml of ethyl acetate
  3. washThe organic phase is washed with 20 ml of water
  4. dry with materialdried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. customAfter a silica column purification, eluent

出典と根拠

ORDレコード
ord-ea07b9d4c47e4ae283c595f0d98262c7
出典データセット
uspto-grants-2015_03
特許番号
US08993565B2

関連ノート

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