Triacetoxyperiodinane → HCID 59765016, compound

HRID 406473Notes

Reaction equation

HRID 406473 reaction equation
[OH:1][C@H:2]1[CH2:6][N:5]([C:7]([N:9]2[CH2:18][CH2:17][C:16]3[N:15]=[CH:14][C:13]([C:19]([F:22])([F:21])[F:20])=[CH:12][C:11]=3[CH2:10]2)=[O:8])[C@H:4]([CH:23]([CH3:25])[CH3:24])[CH2:3]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH:23]([C@H:4]1[N:5]([C:7]([N:9]2[CH2:18][CH2:17][C:16]3[N:15]=[CH:14][C:13]([C:19]([F:21])([F:20])[F:22])=[CH:12][C:11]=3[CH2:10]2)=[O:8])[CH2:6][C:2](=[O:1])[CH2:3]1)([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 159087Triacetoxyperiodinane2×HCID 516892Sodium BicarbonateHCID 59764824HCID 59764824, compound

Product 1

HCID 59765016HCID 59765016, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ((2S,4R)-4-hydroxy-2-isopropyl-pyrrolidin-1-yl)-(3-trifluoromethyl-7,8-dihydro-5H-[1,6]naphthyridin-6-yl)-methanone (prepared as in example #1) (0.118 g, 0.330 mmol) in DCM (4 mL) was added Dess-Martin periodinane (0.210 g, 0.495 mmol). The reaction mixture was stirred at ambient temperature for about 40 min. Additional Dess-Martin reagent (0.303 g, 0.714 mmol) was added in portions over about 4 h and the reaction mixture was stirred for about 16 h. Saturated aqueous sodium bicarbonate (4 mL) was added and the organic portion was separated, dried over MgSO4, filtered, and concentrated to afford (S)-5-isopropyl-1-(3-trifluoromethyl-7,8-dihydro-5H-[1,6]naphthyridine-6-carbonyl)-pyrrolidin-3-one as a sticky yellow solid that was used in subsequent reactions without further purification. RP-HPLC (Table 1, Method d) Rt 2.49 min; m/z: (M+H)+ 356.

Workup

  1. stirringthe reaction mixture was stirred for about 16 h
  2. customthe organic portion was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-77be49d466394ef1acf6dec474d54095
Source dataset
uspto-grants-2014_06
Patent number
US08754107B2

Reaction notes

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