Tetrabutylammonium Fluoride Trihydrate → (+/-)-3-[n,n-Bis(2-hydroxyethyl)amino]-1,2-bis(tetradecanoyloxy)propane

HRID 2191391Notes

Reaction equation

HRID 2191391 reaction equation
O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:39][CH2:40][CH2:41][N:42]([CH2:63][CH:64]([O:82][C:83](=[O:97])[CH2:84][CH2:85][CH2:86][CH2:87][CH2:88][CH2:89][CH2:90][CH2:91][CH2:92][CH2:93][CH2:94][CH2:95][CH3:96])[CH2:65][O:66][C:67](=[O:81])[CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH3:80])[CH2:43][CH2:44][O:45][Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>C1COCC1.C(Cl)Cl>[OH:45][CH2:44][CH2:43][N:42]([CH2:63][CH:64]([O:82][C:83](=[O:97])[CH2:84][CH2:85][CH2:86][CH2:87][CH2:88][CH2:89][CH2:90][CH2:91][CH2:92][CH2:93][CH2:94][CH2:95][CH3:96])[CH2:65][O:66][C:67](=[O:81])[CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH3:80])[CH2:41][CH2:40][OH:39]

Participants

5

Reactant 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 131730103HCID 131730103, compound

Product 1

HCID 91576435(+/-)-3-[n,n-Bis(2-hydroxyethyl)amino]-1,2-bis(tetradecanoyloxy)propaneYield 72%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Another batch of XV was prepared as follows: tetrabutyl ammonium fluride trihydrate (0.50 g, 1.60 mmol) was added to an ice-cooled solution of XIV (0.43 g, 0.40 mmol) in THF (3 mL) under N2 atmosphere. The reaction mixture was allowed to warm up to room temperature. After stirring overnight at room temperature, the reaction mixture was diluted with CH2Cl2 (30 mL) and sequentially washed with 5% NaHCO3 (10 mL), water (10 mL) and saturated aqueous NaCl (10 mL). The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. Purification by column chromatography (SiO2, elution with 2% methanol in CHCl3) furnished XV (172 mg, 72%) as a wax. NMR spectra coordinates are as follows: 1H NMR (CDCl3): δ 5.24-5.14 (m, 1H), 4.35 (dd, J=12.0, 3.2 Hz, 1H), 4.10 (dd, J=12.4, 6.4 Hz, 1H), 3.60 (t, J=5.2 Hz, 4H), 2.77-2.66 (m, 6H), 2.38-2.26 (m, 4H), 1.66-1.54 (m, 4H), 1.36-1.18 (m, 40H), 0.87 (t, J=6.0 Hz, 6H).

Workup

  1. customAnother batch of XV was prepared
  2. washsequentially washed with 5% NaHCO3 (10 mL), water (10 mL) and saturated aqueous NaCl (10 mL)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification
  7. washby column chromatography (SiO2, elution with 2% methanol in CHCl3)

Sources & evidence

ORD record
ord-a1be7d9e93d14ade99ade6048dfc9110
Source dataset
uspto-grants-2012_12
Patent number
US08329681B2

Reaction notes

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