Piperidin-4-ol → 1-Cyclopropylpiperidin-4-ol

HRID 1930212Notes

Reaction equation

HRID 1930212 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(O[C:11]1(O[Si](C)(C)C)[CH2:13][CH2:12]1)C.C([BH3-])#N.[Na+]>CO>[CH:11]1([N:5]2[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]2)[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 79341Piperidin-4-olHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 515828091-Cyclopropylpiperidin-4-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

5 g of 4-hydroxypiperidine were dissolved in methanol. 23.8 mL of 1[(1-ethoxycyclopropyl)oxy]trimethylsilane and 5.8 g of sodium cyano borohydride were added and the mixture was reacted at 60° C. for 12 h. The same amounts of the two reagents were added again and stirring was continued at 60° C. for another 12 h. The mixture was diluted with methanol, filtered over celite and evaporated to dryness. The residue was taken up in ethyl acetate, extracted twice with 2N sodium hydroxide and once with brine, dried over sodium sulfate and evaporated to dryness. The residue was purified by silica gel chromatography to yield 2 g of product 20, MS: 141 (M+)

Workup

  1. customthe mixture was reacted at 60° C. for 12 h
  2. additionThe same amounts of the two reagents were added again
  3. filtrationfiltered over celite
  4. customevaporated to dryness
  5. extractionextracted twice with 2N sodium hydroxide and once with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated to dryness
  8. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-615de8dad020428a8303dff4ec524236
Source dataset
uspto-grants-2012_05
Patent number
US08188117B2

Reaction notes

Loading…