Pyridine, hydrofluoride (1:1) → tert-Butyl 1-(1-hydroxy-2-methylpropan-2-yl)-6-oxo-1,6-dihydropyridin-3-ylcarbamate

HRID 1878721Notes

Reaction equation

HRID 1878721 reaction equation
[Si]([O:8][CH2:9][C:10]([N:13]1[C:18](=[O:19])[CH:17]=[CH:16][C:15]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:14]1)([CH3:12])[CH3:11])(C(C)(C)C)(C)C.N1C=CC=CC=1.F>C(#N)C>[OH:8][CH2:9][C:10]([N:13]1[C:18](=[O:19])[CH:17]=[CH:16][C:15]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:14]1)([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 64774Pyridine, hydrofluoride (1:1)HCID 59843016tert-Butyl 1-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-6-oxo-1,6-dihydropyridin-3-ylcarbamate

Product 1

HCID 69231018tert-Butyl 1-(1-hydroxy-2-methylpropan-2-yl)-6-oxo-1,6-dihydropyridin-3-ylcarbamate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of tert-butyl 1-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-6-oxo-1,6-dihydropyridin-3-ylcarbamate (800 mg, 2017 μmol) in ACN (10 mL) was added hydrogen fluoride pyridine (484 μl, 24206 μmol). The reaction mixture was stirred for 1 h and quenched with dry silica. The solvent was removed under reduced pressure and the product purified on silica (40 g) eluting with 0-5% MeOH/CH2Cl2. MS (ESI pos. ion) m/z (MH+): 283. Calc'd exact mass for C14H22N2O4: 282.

Workup

  1. customquenched with dry silica
  2. customThe solvent was removed under reduced pressure
  3. customthe product purified on silica (40 g)
  4. washeluting with 0-5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-636bd6c503654a95ac004df0be7d807d
Source dataset
uspto-grants-2012_11
Patent number
US08314087B2

Reaction notes

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