Acetic Acid → HCID 45088250, compound

HRID 1642822Notes

Reaction equation

HRID 1642822 reaction equation
[C:1]([CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)#[N:2].C(O[C:12]1(O[Si](C)(C)C)[CH2:14][CH2:13]1)C.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH:12]1([N:6]2[CH2:7][CH2:8][CH:3]([C:1]#[N:2])[CH2:4][CH2:5]2)[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1382234-CyanopiperidineHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 45088250HCID 45088250, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

5.0 g (45.4 mmol) of 4-cyanopiperidine were dissolved in 83 ml of methanol, and 11.9 g (68.1 mmol) of [(1-ethoxy-1-cyclopropyl)oxy]trimethylsilane, 2.9 ml (3.0 g, 49.9 mmol) of acetic acid and 6.0 g (91.0 mmol) of sodium cyanoborohydride were added. The reaction mixture was stirred at 60° C. for 16 h, cooled to RT and then filtered through kieselguhr, the filter cake was washed with methanol and the filtrate was concentrated under reduced pressure. The residue was taken up in ethyl acetate and washed twice with 1 N aqueous sodium hydroxide solution and once with saturated aqueous sodium chloride solution. The organic phase was dried over sodium sulphate, filtered and concentrated under reduced pressure. Yield: 6.0 g (88% of theory)

Workup

  1. temperaturecooled to RT
  2. filtrationfiltered through kieselguhr
  3. washthe filter cake was washed with methanol
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. washwashed twice with 1 N aqueous sodium hydroxide solution and once with saturated aqueous sodium chloride solution
  6. dry with materialThe organic phase was dried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9b7aa7c5eba64520a0048307c36f9741
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

Loading…