(Diethylamino)sulfur trifluoride → Tert-butyl (2-fluoro-2-methylpropyl)carbamate

HRID 81931Notes

Reaction equation

HRID 81931 reaction equation
O[C:2]([CH3:13])([CH3:12])[CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].C(N(S(F)(F)[F:20])CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:20][C:2]([CH3:13])([CH3:12])[CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 11106129tert-Butyl 2-hydroxy-2-methylpropylcarbamate

Product 1

HCID 72698934Tert-butyl (2-fluoro-2-methylpropyl)carbamateYield 79.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A stirred solution of tert-butyl 2-hydroxy-2-methylpropylcarbamate (7.81 g, 41.3 mmol) dissolved in 300 mL of anhydrous CH2Cl2 was cooled to −78° C. under an atmosphere of N2. The reaction mixture was treated with diethylaminosulfur trifloride (DAST) (6.2 mL, 47 mmol) and allowed to warm to ambient temperature overnight. The reaction mixture was treated with saturated NaHCO3 solution and the layers were separated. The organic portion was washed successively with saturated NaHCO3 solution, H2O and brine. The organic portion was dried over Na2SO4, filtered and concentrated under reduced pressure. Chromatography (SiO2, 10% EtOAc/hexanes) gave 6.27 g of tert-butyl 2-fluoro-2-methylpropylcarbamate as an amber oil which solidified on standing.

Workup

  1. temperatureto warm to ambient temperature overnight
  2. customthe layers were separated
  3. washThe organic portion was washed successively with saturated NaHCO3 solution, H2O and brine
  4. dry with materialThe organic portion was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3121fa39df234ee09ca8bb9d34c239bd
Source dataset
uspto-grants-2014_09
Patent number
US08846710B2

Reaction notes

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