Triacetoxyperiodinane → (+/-)-Tert-butyl 1-(3-{[cyclopentyl(4-formylphenyl)acetyl]-amino}benzyl)cyclopropanecarboxylate

HRID 1475655노트

반응식

HRID 1475655 반응식
[CH:1]1([CH:6]([C:27]2[CH:32]=[CH:31][C:30]([CH2:33][OH:34])=[CH:29][CH:28]=2)[C:7]([NH:9][C:10]2[CH:11]=[C:12]([CH:24]=[CH:25][CH:26]=2)[CH2:13][C:14]2([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:16][CH2:15]2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[CH:1]1([CH:6]([C:27]2[CH:32]=[CH:31][C:30]([CH:33]=[O:34])=[CH:29][CH:28]=2)[C:7]([NH:9][C:10]2[CH:11]=[C:12]([CH:24]=[CH:25][CH:26]=2)[CH2:13][C:14]2([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH2:16][CH2:15]2)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

4

반응물 2

HCID 159087TriacetoxyperiodinaneHCID 68170304(+/-)-Tert-butyl 1-[3-({cyclopentyl[4-(hydroxymethyl)phenyl]-acetyl}amino)benzyl]cyclopropanecarboxylate

생성물 1

HCID 86667523(+/-)-Tert-butyl 1-(3-{[cyclopentyl(4-formylphenyl)acetyl]-amino}benzyl)cyclopropanecarboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 4.0 g (8.63 mmol) of (+/−)-tert-butyl 1-[3-({cyclopentyl[4-(hydroxymethyl)phenyl]-acetyl}amino)benzyl]cyclopropanecarboxylate in 20 ml of dichloromethane was cooled to 0° C., and 4.39 g (10.35 mmol) of Dess-Martin reagent [1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one] were added. After the addition had ended, cooling was removed and the reaction mixture was stirred at RT for 3 h. The solution was then diluted with dichloromethane and washed successively with water, saturated sodium carbonate solution and saturated sodium chloride solution. The organic phase was dried with magnesium sulphate and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 50:1→3:1). This gave 2.27 g of the target compound (53.2% of theory).

후처리

  1. additionAfter the addition
  2. temperaturecooling
  3. customwas removed
  4. additionThe solution was then diluted with dichloromethane
  5. washwashed successively with water, saturated sodium carbonate solution and saturated sodium chloride solution
  6. dry with materialThe organic phase was dried with magnesium sulphate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 50:1→3:1)

출처 및 근거

ORD 기록
ord-d8cffbed6c934026bbba486b83cde5ec
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018258B2

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