Triacetoxyperiodinane → HCID 68171040, compound

HRID 1429080Notes

Reaction equation

HRID 1429080 reaction equation
[C:1]([O:5][C:6]([N:8]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C@:9]1([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:11][C@H:10]1[CH2:12][CH:13]([OH:18])[CH2:14][CH2:15][CH:16]=[CH2:17])=[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]([C:24]([O:26][C:27]([CH3:28])([CH3:30])[CH3:29])=[O:25])[C@:9]1([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:11][C@H:10]1[CH2:12][C:13](=[O:18])[CH2:14][CH2:15][CH:16]=[CH2:17])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 68171039HCID 68171039, compound

Product 1

HCID 68171040HCID 68171040, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1R,2S)-ethyl 1-(bis(tert-butoxycarbonyl)amino)-2-(2-hydroxyhex-5-enyl)cyclopropanecarboxylate (4.3 g, 10 mmol) in dichloromethane (50 ml) at 25° C. was added Dess-Martin Periodinane (5.97 g, 14.1 mmol). The reaction mixture was stirred for 3 h and quenched with 1 N aqueous sodium thiosulfate solution (50 mL) and saturated aqueous sodium bicarbonate solution (15 mL), and the reaction mixture stirred for 1 h. The organic layer was separated, dried over anhydrous sodium sulfate, filtered, and evaporated under reduced. The crude product was purified by flash chromatography on silica gel (15% ethyl acetate/hexane) to provide (1R,2S)-ethyl 1-(bis(tert-butoxycarbonyl)amino)-2-(2-oxohex-5-enyl)cyclopropane carboxylate (3.8 g, 88% yield) as an oil. MS (ESI): m/z=448.1 [M+Na].

Workup

  1. customquenched with 1 N aqueous sodium thiosulfate solution (50 mL) and saturated aqueous sodium bicarbonate solution (15 mL)
  2. stirringthe reaction mixture stirred for 1 h
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by flash chromatography on silica gel (15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-51cbf0c16c084d0e91ca7c9db88c20f5
Source dataset
uspto-grants-2015_01
Patent number
US08937041B2

Reaction notes

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