Triacetoxyperiodinane → HCID 178482002, compound

HRID 1960007Notes

Reaction equation

HRID 1960007 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-1288b7f9c0b34175927d5f40aa321401
Source dataset
uspto-grants-2013_04
Patent number
US08410275B2

Reaction notes

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