Triacetoxyperiodinane → (S)-4-[2-(3-fluoro-2-methyl-benzyl)-1-phenyl-indolizine-3-carbonyl]-2-(2-oxo-ethyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1963063Notes

Reaction equation

HRID 1963063 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[N:24]3[C:19]([CH:20]=[CH:21][CH:22]=[CH:23]3)=[C:18]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:17]=2[CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[C:33]=2[CH3:39])=[O:15])[CH2:10][C@@H:9]1[CH2:40][CH2:41][OH:42])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>C(Cl)Cl.C(OCC)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[N:24]3[C:19]([CH:20]=[CH:21][CH:22]=[CH:23]3)=[C:18]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:17]=2[CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[C:33]=2[CH3:39])=[O:15])[CH2:10][C@@H:9]1[CH2:40][CH:41]=[O:42])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67773585(S)-4-[2-(3-fluoro-2-methyl-benzyl)-1-phenyl-indolizine-3-carbonyl]-2-(2-hydroxy-ethyl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86670666(S)-4-[2-(3-fluoro-2-methyl-benzyl)-1-phenyl-indolizine-3-carbonyl]-2-(2-oxo-ethyl)-piperazine-1-carboxylic acid tert-butyl esterYield 101.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound of example 5, step 5 (0.955 g, 1.67 mmol) in 10 ml of DCM under argon was added 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (7.78 g, 1.84 mmol). The mixture was stirred at room temperature for 3.5 h and then diluted with 40 ml of diethyl ether. The solution was washed three times with a 1 N solution of sodium hydroxide (15 ml) and twice with brine (15 ml). The organic phase was dried over sodium sulfate, filtered and evaporated to dryness under reduced pressure to give 0.965 g of the title compound as a green powder which was directly used in the next step.

Workup

  1. washThe solution was washed three times with a 1 N solution of sodium hydroxide (15 ml)
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-9d8461e9622746b6b3619e8acc2be74d
Source dataset
uspto-grants-2013_04
Patent number
US08415336B2

Reaction notes

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