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

HRID 882588노트

반응식

HRID 882588 반응식
[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

참가 물질

7

반응물 4

HCID 6382DibromodifluoromethaneHCID 14797Potassium Hydroxide2회HCID 9989226AluminaHCID 68310878(2S)-1-(benzylsulphonyl)-3-phenylpropan-2-amine

생성물 1

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

시약·촉매·용매 2

HCID 2631-Butanol용매HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2a756f9b74224f8093ddb93c0dac91ed
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08992932B2

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