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

HRID 1475655Notes

Reaction equation

HRID 1475655 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-d8cffbed6c934026bbba486b83cde5ec
Source dataset
uspto-grants-2015_04
Patent number
US09018258B2

Reaction notes

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