2,6-Lutidine → HCID 20740326, compound

HRID 1883162Notes

Reaction equation

HRID 1883162 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]N1C(=O)CCC1=O.[C:28]([N:38]([CH2:42][CH2:43][OH:44])[CH2:39][CH2:40]O)([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29].N1C(C)=CC=CC=1C.O([Si:61]([CH:68]([CH3:70])[CH3:69])([CH:65]([CH3:67])[CH3:66])[CH:62]([CH3:64])[CH3:63])S(C(F)(F)F)(=O)=O>C(Cl)Cl.O>[CH2:31]([O:30][C:28](=[O:29])[N:38]([CH2:39][CH2:40][Br:20])[CH2:42][CH2:43][O:44][Si:61]([CH:68]([CH3:70])[CH3:69])([CH:65]([CH3:67])[CH3:66])[CH:62]([CH3:64])[CH3:63])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

8

Reactant 5

HCID 79372,6-LutidineHCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 23498447HCID 23498447, compound

Product 1

HCID 20740326HCID 20740326, compoundYield 20.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Triphenylphosphine (1.15 g, 4.39 mmol) and N-bromosuccinimide (0.79 g, 4.39 mmol) were added to a 0° C. solution of N-Cbz-diethanolamine (1 g, 4.18 mmol) in 40 ml of methylene chloride. The reaction was stirred at room temperature for 4 hours and then cooled to 0° C. 2,6-Lutidine (0.97 ml, 8.36 mmol) was added, followed by the dropwise addition of triisopropylsilyl triflate (1.35 ml, 5 mmol). The reaction was stirred at room temperature for 12 h, diluted with water, and concentrated under vacuum and the residue was extracted with ethyl acetate (2×50 ml). The organic layer was washed with 0.5 M HCl, saturated sodium bicarbonate, brine and dried over sodium sulfate. Evaporation of the solvent followed by chromatography (SiO2 Biotage 40 M, 3%-5% ethyl acetate/hexanes) gave (2-bromo-ethyl)-(2-triisopropylsilanyloxy-ethyl)-carbamic acid benzyl ester (400 mg) as a clear oil.

Workup

  1. temperaturecooled to 0° C
  2. stirringThe reaction was stirred at room temperature for 12 h
  3. concentrationconcentrated under vacuum
  4. extractionthe residue was extracted with ethyl acetate (2×50 ml)
  5. washThe organic layer was washed with 0.5 M HCl, saturated sodium bicarbonate, brine
  6. dry with materialdried over sodium sulfate
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-dcc79e61cccf47c08cc3fbe0fba52563
Source dataset
uspto-grants-2004_07
Patent number
US06759428B2

Reaction notes

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