Water → (5-Hydroxymethyl-6-methyl-pyridin-2-yl)-carbamic acid tert-butyl ester

HRID 1789859Notes

Reaction equation

HRID 1789859 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]([O:23][C:24](=[O:42])[NH:25][C:26]1[CH:31]=[CH:30][C:29]([C:32](C)(C)[O:33][SiH2]C(C)(C)C)=[C:28]([CH3:41])[N:27]=1)([CH3:22])([CH3:21])[CH3:20].O>C1COCC1>[C:19]([O:23][C:24](=[O:42])[NH:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][OH:33])=[C:28]([CH3:41])[N:27]=1)([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 131725830tert-butyl N-[5-(2-tert-butylsilyloxypropan-2-yl)-6-methyl-2-pyridinyl]carbamate

Product 1

HCID 53997211(5-Hydroxymethyl-6-methyl-pyridin-2-yl)-carbamic acid tert-butyl esterYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (19.6 g, 62.4 mmol) was added to a solution of [5-(tert-butyl-dimethyl-silanyloxymethyl)-6-methyl-pyridin-2-yl]-carbamic acid tert-butyl ester (10.5 g, 31.23 mmol) in THF (100 mL) and stirred at room temperature overnight. Water was added and the product extracted with chloroform. The organic phase was dried and concentrated under reduced pressure. Flash chromatography (MeOH/CH2Cl2, 2.5:77.5) gave (5-hydroxymethyl-6-methyl-pyridin-2-yl)-carbamic acid tert-butyl ester (6.0 g, 81%).

Workup

  1. extractionthe product extracted with chloroform
  2. customThe organic phase was dried
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1373f99ac6324b0db02b48761b5136e7
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

Loading…