Triacetoxyperiodinane → HCID 178482002, compound

HRID 1518051Notes

Reaction equation

HRID 1518051 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]([CH:62]=[C:63]([C:65]([F:68])([F:67])[F:66])[CH:64]=1)[CH2:28][N:29]([CH2:36][C:37]1[C:38]([N:49]2[CH2:53][CH2:52][CH2:51][C@@H:50]2[C@H:54]2[CH2:59][CH2:58][C@H:57]([CH2:60][OH:61])[CH2:56][CH2:55]2)=[N:39][C:40]2[C:45]([CH:46]=1)=[CH:44][C:43]([F:47])=[C:42]([F:48])[CH:41]=2)[C:30]1[N:31]=[N:32][N:33]([CH3:35])[N:34]=1>C(Cl)Cl>[F:67][C:65]([F:66])([F:68])[C:63]1[CH:62]=[C:27]([CH:26]=[C:25]([C:24]([F:23])([F:69])[F:70])[CH:64]=1)[CH2:28][N:29]([CH2:36][C:37]1[C:38]([N:49]2[CH2:53][CH2:52][CH2:51][C@@H:50]2[C@H:54]2[CH2:55][CH2:56][C@H:57]([CH:60]=[O:61])[CH2:58][CH2:59]2)=[N:39][C:40]2[C:45]([CH:46]=1)=[CH:44][C:43]([F:47])=[C:42]([F:48])[CH:41]=2)[C:30]1[N:31]=[N:32][N:33]([CH3:35])[N:34]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 178482003HCID 178482003, compound

Product 1

HCID 178482002HCID 178482002, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinate (4.07 g, 9.6 mmol) is added to a suspension of trans-(4-{(R)-1-[3-({N-[3,5-bis(trifluoromethyl)benzyl]-N-(2-methyl-2H-tetrazol-5-yl)amino}methyl)-6,7-difluoroquinolin-2-yl]pyrrolidin-2-yl}cyclohexyl)methanol (6.25 g, 9.1 mmol) in CH2Cl2 (75 mL) at 0° C., and the resulting mixture is stirred at room temperature for 20 min. The reaction mixture is quenched by addition of sat. NaHCO3 aq. and extracted with CH2Cl2. The combined organic layer is washed with brine, dried over magnesium sulfate, filtered and concentrated. The crude product is purified by silica gel column chromatography to give trans-4-{(R)-1-[3-({N-[3,5-bis(trifluoromethyl)benzyl]-N-(2-methyl-2H-tetrazol-5-yl)amino}methyl)-6,7-difluoroquinolin-2-yl]pyrrolidin-2-yl}cyclohexanecarbardehyde.

Workup

  1. customThe reaction mixture is quenched by addition of sat. NaHCO3 aq.
  2. extractionextracted with CH2Cl2
  3. washThe combined organic layer is washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product is purified by silica gel column chromatography
  8. customto give trans-4-{(R)-1-[3-({N-[3,5-bis(trifluoromethyl)benzyl]-N-(2-methyl-2H-tetrazol-5-yl)amino}methyl)-6,7-difluoroquinolin-2-yl]pyrrolidin-2-yl}cyclohexanecarbardehyde

Sources & evidence

ORD record
ord-8f9ddbe61d37449d8c1b39911ef4a3fc
Source dataset
uspto-grants-2012_07
Patent number
US08232403B2

Reaction notes

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