Pyridine → tert-butyl N-(2-methyl-4-oxobutan-2-yl)carbamate

HRID 1795997Notes

Reaction equation

HRID 1795997 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][C:8]([CH3:13])([CH3:12])[CH2:9][CH2:10][OH:11])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.N1C=CC=CC=1>CS(C)=O.[Cl-].[Na+].O>[C:1]([O:5][C:6](=[O:14])[NH:7][C:8]([CH3:13])([CH3:12])[CH2:9][CH:10]=[O:11])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 1049PyridineHCID 8471TriethylamineHCID 15473340tert-Butyl (4-hydroxy-2-methylbutan-2-yl)carbamate

Product 1

HCID 11788901tert-butyl N-(2-methyl-4-oxobutan-2-yl)carbamate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
25 °C

Procedure

(3-Hydroxy-1,1-dimethyl-propyl)-carbamic acid tert-butyl ester (9.8 g, 0.048 mol) was dissolved in DMSO (160 mL). The solution was treated with Et3N (20.2 mL, 0.145 mol) followed by a solution of pyridine sufurtrioxide complex (23.2 g, 0.145 mol) in DMSO (160 mL). Upon complete addition, the solution was stirred for 1 h at 25° C. The mixture was diluted with brine and extracted with Et2O (3×125 mL). The organic phase was washed with 10% citric acid(aq), saturated NaHCO3 and brine. The organic phase was dried (MgSO4) and concentrated to the desired material as a yellow oil (8.3 g, 56%): 1H NMR (DMSO-d6) δ 9.67 (t, 1H, J=3 Hz), 2.66 (s, 2H), 1.37 (s, 9H), 1.28 (s, 6H).

Workup

  1. additionUpon complete addition
  2. extractionextracted with Et2O (3×125 mL)
  3. washThe organic phase was washed with 10% citric acid(aq), saturated NaHCO3 and brine
  4. dry with materialThe organic phase was dried (MgSO4)
  5. concentrationconcentrated to the desired material as a yellow oil (8.3 g, 56%)

Sources & evidence

ORD record
ord-3e176263b8d148e2a98658a013bf10b0
Source dataset
uspto-grants-2006_04
Patent number
US07030118B2

Reaction notes

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