Triacetoxyperiodinane → HCID 86606926, compound

HRID 747033Notes

Reaction equation

HRID 747033 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[F:23][C:24]([F:64])([F:63])[C:25]1[CH:26]=[C:27]([C@H:35]([O:37][C@@H:38]2[C@@H:43]([C:44]3[CH:49]=[CH:48][C:47]([F:50])=[CH:46][CH:45]=3)[C@H:42]([CH2:51][N:52]3[CH2:62][CH2:61][C:55]4([CH2:59][O:58][CH2:57][C@H:56]4[OH:60])[CH2:54][CH2:53]3)[CH2:41][CH2:40][O:39]2)[CH3:36])[CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1>ClCCl>[F:64][C:24]([F:23])([F:63])[C:25]1[CH:26]=[C:27]([C@H:35]([O:37][C@@H:38]2[C@@H:43]([C:44]3[CH:49]=[CH:48][C:47]([F:50])=[CH:46][CH:45]=3)[C@H:42]([CH2:51][N:52]3[CH2:53][CH2:54][C:55]4([CH2:59][O:58][CH2:57][C:56]4=[O:60])[CH2:61][CH2:62]3)[CH2:41][CH2:40][O:39]2)[CH3:36])[CH:28]=[C:29]([C:31]([F:32])([F:33])[F:34])[CH:30]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86606927HCID 86606927, compound

Product 1

HCID 86606926HCID 86606926, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (0.6 g, 1.4 mmol) was added to a solution of (4S)-8-[(2R,3R,4R)-2-[(1R)-1-(3,5-bis(trifluoromethyl)phenyl)ethoxy]-3-(4-fluorophenyl)-tetrahydropyran-4-yl]methyl-2-oxa-8-aza-spiro[4.5]decan-4-ol (Example 3; 0.85 g, 1.4 mmol) in dichloromethane (20 ml). The mixture was stirred at room temperature for 4 hours then quenched by addition of saturated sodium hydrogen carbonate. After 30 minutes the mixture was partitioned between water and dichloromethane. The organic extracts were dried and concentrated. The residue was chromatographed on silica gel eluting with 2% methanol/dichloromethane to give the title compound (510 mg, 60%).

Workup

  1. customthen quenched by addition of saturated sodium hydrogen carbonate
  2. customAfter 30 minutes the mixture was partitioned between water and dichloromethane
  3. customThe organic extracts were dried
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel eluting with 2% methanol/dichloromethane

Sources & evidence

ORD record
ord-ec234aabfae849088b1dedbc97d608c5
Source dataset
uspto-grants-2008_07
Patent number
US07393858B2

Reaction notes

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