Triacetoxyperiodinane → HCID 25008472, compound

HRID 2093199Notes

Reaction equation

HRID 2093199 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[F:23][C:24]([F:70])([F:69])[C:25]1[CH:26]=[C:27]([C@H:35]2[O:39][C:38](=[O:40])[N:37]([CH2:41][C:42]3[CH:47]=[C:46]([C:48]([F:51])([F:50])[F:49])[CH:45]=[CH:44][C:43]=3[C:52]3[C:57]([Cl:58])=[CH:56][CH:55]=[C:54]([C:59]4[CH:64]=[CH:63][C:62]([CH2:65][OH:66])=[CH:61][C:60]=4[CH3:67])[CH:53]=3)[C@H:36]2[CH3:68])[CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1.CCOC(C)=O.CCCCCC>C(Cl)Cl>[F:70][C:24]([F:23])([F:69])[C:25]1[CH:26]=[C:27]([C@H:35]2[O:39][C:38](=[O:40])[N:37]([CH2:41][C:42]3[CH:47]=[C:46]([C:48]([F:49])([F:51])[F:50])[CH:45]=[CH:44][C:43]=3[C:52]3[CH:53]=[C:54]([C:59]4[CH:64]=[CH:63][C:62]([CH:65]=[O:66])=[CH:61][C:60]=4[CH3:67])[CH:55]=[CH:56][C:57]=3[Cl:58])[C@H:36]2[CH3:68])[CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 21226206Ethyl acetate hexaneHCID 25008470HCID 25008470, compound

Product 1

HCID 25008472HCID 25008472, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin Periodinane (145 mg, 0.34 mmol) was added to a solution of alcohol from Example 49 (200 mg, 0.285 mmol) in methylene chloride (5 ml) at room temperature. The resulting slurry was stirred at room temperature for 1 h. No starting material was seen by TLC (EtOAc/hexane 2:8). The solid was filtered. The filtrate was concentrated. The residue was purified by flash column on silica gel, eluting with EtOAc/hexane (30:70) to give the title compound as a colorless solid. 1H NMR (CDCl3, 500 MHz): δ a mixture of 6:4 atopoisomers 10.03 (s, 1H), 7.90 (s, 2/5H), 7.89 (s, 3/5H), 7.83 (s, 1H), 7.78 (d, J=8.0 Hz, 3/5H), 7.75 (d, J=8.0 Hz, 2/5 H), 7.74 (s, 1.2H), 7.73 (s, 0.8H), 7.72 (s, 2/5H), 7.70 (s, 3/5H), 7.64 (d, J=8.0 Hz, 1H), 7.52 (d, J=8.0 Hz, 3/5H), 7.47 (d, J=8.0 Hz, 2/5H), 7.46 (d, J=8.0 Hz, 3/5H), 7.43 (d, J=8.0 Hz, 2/5H),7.40 (m, 1H), 7.28 (m, 1.5H), 7.23 (d, J=2.0 Hz, 0.5H), 5.64 (d, J=8.0 Hz, 1H), 5.04 (d, J=15.5 Hz, 3/5H), 4.83 (d, J=16 Hz, 2/5H), 4.09 (d, J=16 Hz, 2/5H), 4.01 (d, J=15.0 Hz, 3/5H), 4.00 (m, 2/5H), 3.91 (m, 3/5H), 2.43 (s, 1.8H), 2.41 (s, 1.2H), 0.65 (d, J=6.5 Hz, 1.8H), 0.61 (d, J=7.0 Hz, 1.2H).

Workup

  1. filtrationThe solid was filtered
  2. concentrationThe filtrate was concentrated
  3. customThe residue was purified by flash column on silica gel
  4. washeluting with EtOAc/hexane (30:70)

Sources & evidence

ORD record
ord-cd9a895c27f34173a0448520c6e92db7
Source dataset
uspto-grants-2013_05
Patent number
US08440702B2

Reaction notes

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