Acetic Acid → HCID 11217927, compound

HRID 709398Notes

Reaction equation

HRID 709398 reaction equation
[BH3-]C#N.[Na+].C(O)(=O)C.[C:9]([O:13][C:14]([NH:16][N:17]=[CH:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:15])([CH3:12])([CH3:11])[CH3:10]>C1COCC1>[C:9]([O:13][C:14]([NH:16][NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:15])([CH3:12])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 72828588HCID 72828588, compound

Product 1

HCID 11217927HCID 11217927, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

6.65 g of NaBH3CN are solubilized in acetic acid (10.5 g; 175 mmoles). The solution is cooled at 0° C. and a solution in anhydrous THF (35 mL; 0.15 M) of t-butyl-2-pentylidenhydrazincarboxylate (7.00 g; 35 mmoles) prepared in example 11a is dropwise added. The reaction mixture is then let to warm to room temperature under stirring for 24 hours. The organic phase is washed with a 10% NaHCO3 solution and then extracted with chloroform. The organic phase is recovered and the solvent removed under vacuum. The obtained residue is purified by chromatography on silica gel using as eluent a chloroform/methanol 90:1 volume/volume mixture. 6.3 g of t-butyl-2-pentylhydrazincarboxylate are obtained (white solid; yield 90%).

Workup

  1. additionis dropwise added
  2. temperatureto warm to room temperature
  3. washThe organic phase is washed with a 10% NaHCO3 solution
  4. extractionextracted with chloroform
  5. customThe organic phase is recovered
  6. customthe solvent removed under vacuum
  7. customThe obtained residue is purified by chromatography on silica gel using as eluent a chloroform/methanol 90:1 volume/volume mixture

Sources & evidence

ORD record
ord-ab2a2ad8551042189be2913ce269202c
Source dataset
uspto-grants-2015_11
Patent number
US09181196B2

Reaction notes

Loading…