Triacetoxyperiodinane → 4-(1-benzenesulfonyl-5-fluoro-1H-indole-2-carbonyl)-4-propyl-piperidine-1-carboxylic acid tert-butyl ester

HRID 661568Notes

Reaction equation

HRID 661568 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH:17]([C:19]2[N:20]([S:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)(=[O:31])=[O:30])[C:21]3[C:26]([CH:27]=2)=[CH:25][C:24]([F:28])=[CH:23][CH:22]=3)[OH:18])([CH2:14][CH2:15][CH3:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([C:17]([C:19]2[N:20]([S:29]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)(=[O:31])=[O:30])[C:21]3[C:26]([CH:27]=2)=[CH:25][C:24]([F:28])=[CH:23][CH:22]=3)=[O:18])([CH2:14][CH2:15][CH3:16])[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 666875264-[(1-benzenesulfonyl-5-fluoro-1H-indol-2-yl)-hydroxy-methyl]4-propyl-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 666881904-(1-benzenesulfonyl-5-fluoro-1H-indole-2-carbonyl)-4-propyl-piperidine-1-carboxylic acid tert-butyl esterYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[(1-benzenesulfonyl-5-fluoro-1H-indol-2-yl)-hydroxy-methyl]-4-propyl-piperidine-1-carboxylic acid tert-butyl ester (319 mg, 0.6 mmol) in 20 mL of dichloromethane was added Dess-Martin periodinane (255 mg, 0.6 mmol). The reaction was stirred for 30 minutes at room temperature, and then quenched with a 1:1 mixture of 5% aqueous Na2S2O3: saturated aqueous NaHCO3. The mixture was stirred until all solids were dissolved, then extracted with diethyl ether. The combined organic layers were washed with saturated aqueous NaHCO3, and brine, dried (MgSO4), filtered and concentrated in vacuo to afford crude 4-(1-benzenesulfonyl-5-fluoro-1H-indole-2-carbonyl)-4-propyl-piperidine-1-carboxylic acid tert-butyl ester (300 mg, 0.57 mmol) as a beige solid in a 95% yield.

Workup

  1. customquenched with a 1:1 mixture of 5% aqueous Na2S2O3
  2. stirringThe mixture was stirred until all solids
  3. dissolutionwere dissolved
  4. extractionextracted with diethyl ether
  5. washThe combined organic layers were washed with saturated aqueous NaHCO3, and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2780224ac4394282863de926769adf25
Source dataset
uspto-grants-2011_12
Patent number
US08084623B2

Reaction notes

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