Triacetoxyperiodinane → HCID 86586684, compound

HRID 2088152Notes

Reaction equation

HRID 2088152 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([CH2:13][O:14][C@@H:15]2[CH2:21][CH2:20][C@@H:19]3[NH:22][C@@:16]2([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:17][C@H:18]3[CH2:23][OH:24])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])(O)=O.[Na+].C(=O)([O-])O.[Na+]>ClCCl>[F:11][C:9]([F:10])([F:12])[C:7]1[CH:6]=[C:5]([CH2:13][O:14][C@@H:15]2[CH2:21][CH2:20][C@@H:19]3[NH:22][C@@:16]2([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:17][C@H:18]3[CH:23]=[O:24])[CH:4]=[C:3]([C:2]([F:1])([F:31])[F:32])[CH:8]=1

Participants

6

Reactant 4

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 23665763Sodium BisulfiteHCID 86586671HCID 86586671, compound

Product 1

HCID 86586684HCID 86586684, compoundYield 108.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1R*,2R*,5S*,6R*)-2-{[3,5-Bis(trifluoromethyl)phenyl]methoxy}-6-hydroxymethyl-1-phenyl-8-azabicyclo[3.2.1]octane (Example 29; 1.38 g, 2.5 mmol) in dichloromethane (6 ml) at room temperature was treated with Dess-Martin periodinane (1.07 g, 2.5 mmol) and stirred for 1 hour. The mixture was treated with 5% sodium hydrogen sulfite (50 ml) and saturated sodium hydrogen carbonate (30 ml) and stirred for 5 minutes. The organics were collected, washed with brine, dried (MgSO4) and concentrated in vacuo to afford the title compound as a yellow foam (1.24 g, 91%).

Workup

  1. stirringstirred for 5 minutes
  2. customThe organics were collected
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0dba7625b00d429599b6a5ae41627c77
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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