Triethylamine → HCID 66975214, compound

HRID 1022567Notes

Reaction equation

HRID 1022567 reaction equation
[CH2:1]([NH:8][CH2:9][CH:10]([CH2:21][OH:22])[CH:11]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([F:20])[CH:14]=1)[OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:30]([Si:34](Cl)([CH3:36])[CH3:35])([CH3:33])([CH3:32])[CH3:31]>C1COCC1>[CH2:1]([NH:8][CH2:9][CH:10]([CH2:21][O:22][Si:34]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:36])[CH3:35])[CH:11]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([F:20])[CH:14]=1)[OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 66976007HCID 66976007, compound

Product 1

HCID 66975214HCID 66975214, compoundYield 48.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (1RS,2SR)-2-[(benzylamino)methyl]-1-(4-chloro-3-fluorophenyl)propane-1,3-diol (44.5 g) and triethylamine (21.1 ml) in THF (416 mL) was added a solution of tert-butylchlorodimethylsilane (22.8 g) in THF (42 mL) under ice-cooling, and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate. The diluted solution was washed with distilled water and brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (NH, hexane/ethyl acetate) to give the title compound (29.3 g).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was diluted with ethyl acetate
  4. washThe diluted solution was washed with distilled water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (NH, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-96d3882cfc93422c8a13b39e5d19c5db
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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