Dibromodifluoromethane → (2S,3E)-1,4-diphenylbut-3-en-2-amine

HRID 882588ノート

反応式

HRID 882588 の反応式
[OH-].[K+].[O-2].[Al+3].[O-2].[O-2].[Al+3].C(S([CH2:18][C@@H:19]([NH2:27])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=O)=O)C1C=CC=CC=1.BrC(Br)(F)F>CO.C(O)CCC>[C:21]1([CH2:20][C@H:19]([NH2:27])/[CH:18]=[CH:20]/[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

参加物

7

反応物 4

HCID 6382DibromodifluoromethaneHCID 14797Potassium Hydroxide2 回HCID 9989226AluminaHCID 68310878(2S)-1-(benzylsulphonyl)-3-phenylpropan-2-amine

生成物 1

HCID 68309085(2S,3E)-1,4-diphenylbut-3-en-2-amine

試薬・触媒・溶媒 2

HCID 2631-Butanol溶媒HCID 887Methanol溶媒

実験手順

552.7 mg (9.85 mmol) of potassium hydroxide were dissolved in methanol, adsorbed onto 1.1 g of neutral aluminium oxide and then dried under high vacuum. To a solution of 240 mg (0.82 mmol) of (2S)-1-(benzylsulphonyl)-3-phenylpropan-2-amine and 1.56 g of the potassium hydroxide on aluminium oxide thus prepared in 6.2 ml of n-butanol were added dropwise, at 5-10° C., 307 μl (3.3 mmol) of dibromodifluoromethane. The reaction mixture was stirred at RT for 2 h, then filtered through Celite, and the residue was washed thoroughly with dichloromethane. The filtrate was concentrated and the resulting residue was dried under reduced pressure. The crude product thus obtained was purified by means of preparative HPLC. 98 mg (35% of theory) of the title compound were obtained with an E/Z diastereomer ratio of 4:1.

後処理

  1. customdried under high vacuum
  2. additionwere added dropwise, at 5-10° C.
  3. filtrationfiltered through Celite
  4. washthe residue was washed thoroughly with dichloromethane
  5. concentrationThe filtrate was concentrated
  6. customthe resulting residue was dried under reduced pressure
  7. customThe crude product thus obtained
  8. customwas purified by means of preparative HPLC

出典と根拠

ORDレコード
ord-2a756f9b74224f8093ddb93c0dac91ed
出典データセット
uspto-grants-2015_03
特許番号
US08992932B2

反応ノート

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