Lauric Acid → HCID 18989543, compound

HRID 2395711Notes

Reaction equation

HRID 2395711 reaction equation
[C:1]([OH:14])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(Cl)(=O)C(Cl)=O.[Si:21]([O:28][CH:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].C(N(CC)CC)C>C(Cl)Cl.CN(C)C=O>[O:14]=[C:1]([N:32]1[CH2:33][CH2:34][CH:29]([O:28][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:22])[CH3:23])[CH2:30][CH2:31]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

7

Reactant 4

HCID 3893Lauric AcidHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 114813284-((Tert-butyldimethylsilyl)oxy)piperidine

Product 1

HCID 18989543HCID 18989543, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

Dissolve lauric acid (0.77 g) in methylene chloride (50 mL) and cool to 0° C. Add oxalyl chloride (0.37 mL) and dimethylformamide (3 drops). Allow to warm to room temperature and stir for 1 hour. Add this solution to a mixture off 4-(O-tert-butyldimethylsilyloxy)piperidine and triethylamine (1 mL) in methylene chloride (25 mL). Heat at reflux overnight. Dilute with methylene chloride (50 mL) and separate the organic phase. Wash twice with 10% sodium hydroxide, once with water, and once with brine. Dry (Na2SO4) and evaporate the solvent in vacuo. Dissolve the residue in hexane (100 mL) and wash twice with 10% hydrochloric acid (50 mL), once with saturated sodium hydrogen carbonate and once with brine. Dry (Na2SO4) and evaporate the solvent in vacuo to give 1-oxododecyl-4-(O-tert-butyldimethylsilyloxy)piperidine.

Workup

  1. temperatureAllow to warm to room temperature
  2. temperatureHeat
  3. temperatureat reflux overnight
  4. customseparate the organic phase
  5. washWash twice with 10% sodium hydroxide, once with water
  6. dry with materialDry (Na2SO4)
  7. customevaporate the solvent in vacuo
  8. dissolutionDissolve the residue in hexane (100 mL)
  9. washwash twice with 10% hydrochloric acid (50 mL), once with saturated sodium hydrogen carbonate and once with brine
  10. dry with materialDry (Na2SO4)
  11. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-f0c3fddd1707435fbb9f9ea6a1c6e1cf
Source dataset
uspto-grants-1996_02
Patent number
US05489600

Reaction notes

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