1,1-Dichloroethane → HCID 66592460, compound

HRID 1091305Notes

Reaction equation

HRID 1091305 reaction equation
[CH2:1]([O:8][C:9](=[O:17])[N:10]([CH2:14][CH:15]=O)[CH2:11][CH:12]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:19][C:20]([NH2:24])([CH3:23])[CH2:21][F:22].ClC(Cl)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(=O)([O-])O.[Na+]>[CH2:1]([O:8][C:9]([N:10]1[CH2:14][CH2:15][N:24]([C:20]([CH3:23])([CH3:19])[CH2:21][F:22])[CH2:12][CH2:11]1)=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 63651,1-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 139352511-Fluoro-2-methylpropan-2-amine hydrochlorideHCID 15009275Benzyl Bis(2-oxoethyl)carbamate

Product 1

HCID 66592460HCID 66592460, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Bis-(2-oxoethyl)carbamic acid benzyl ester (0.81 g, 3.45 mmol) and 1,1-dimethyl-2-fluoroethylamine hydrochloride (0.40 g, 3.14 mmol) were dissolved dichloroethane (50 mL), and sodium triacetoxyborohydride (1.99 g, 9.41 mmol) was added thereto. The mixture was stirred for three days at room temperature. A saturated aqueous solution of sodium hydrogen carbonate (20 mL) was added to the reaction liquor, and the mixture was stirred for 30 minutes, and then extracted with methylenechloride. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and then the solvent was concentrated under reduced pressure. The obtained residue was purified by flash chromatography (Flash Chromatography System from Biotage AB, column size: 40S, n-hexane/ethyl acetate=1/1 to ethyl acetate), to obtain the title compound (370 mg, 29%), partially including impurities, as an oily matter.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred for 30 minutes
  3. extractionextracted with methylenechloride
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationthe solvent was concentrated under reduced pressure
  7. customThe obtained residue was purified by flash chromatography (Flash Chromatography System from Biotage AB, column size: 40S, n-hexane/ethyl acetate=1/1 to ethyl acetate)

Sources & evidence

ORD record
ord-9db10dbdb57a4f0cbb6198c1d3ebaec6
Source dataset
uspto-grants-2012_03
Patent number
US08129366B2

Reaction notes

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