Dimethylformamide → HCID 23121940, compound

HRID 1713502Notes

Reaction equation

HRID 1713502 reaction equation
O=[CH:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].CN(C)C=O.[NH:17]1[CH2:22][CH:21]=[CH:20][CH2:19][CH2:18]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(OCC)(=O)C.O1CCCC1>[N:17]1([CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH2:18][CH:19]=[CH:20][CH2:21][CH2:22]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 127501,2,3,6-TetrahydropyridineHCID 4247255tert-butyl N-(2-oxoethyl)carbamateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 23121940HCID 23121940, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 1,1-dimethylethyl N-(2-oxoethyl)carbamate (2.0 g, 13 mmol) were added N,N-dimethylformamide (50 mL), tetrahydrofuran (50 mL), 1,2,3,6-tetrahydropyridine (1.2 mL, 13 mmol) and sodium triacetoxyborohydride (5.3 g, 25 mmol), and the mixture was stirred at room temperature for 14 hours. To the reaction solution was added ethyl acetate, and the resulting mixture was washed with a 0.5 M aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (ethyl acetate to ethyl acetate:methanol=8:2) and further purified with amino silica gel column chromatography (hexane:ethyl acetate=9:1 to ethyl acetate) to obtain the title compound (1.2 g, yield 41%).

Workup

  1. washthe resulting mixture was washed with a 0.5 M aqueous sodium hydrogen carbonate solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified with silica gel column chromatography (ethyl acetate to ethyl acetate:methanol=8:2)
  5. customfurther purified with amino silica gel column chromatography (hexane:ethyl acetate=9:1 to ethyl acetate)

Sources & evidence

ORD record
ord-b6a55f42ad5f4a0094f6f6359df36e95
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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