Triethylamine → HCID 66975486, compound

HRID 1022560Notes

Reaction equation

HRID 1022560 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]([F:19])=[C:15]([Cl:20])[CH:14]=1)[OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]([Si:27](Cl)([CH3:29])[CH3:28])([CH3:26])([CH3:25])[CH3:24].C(N(CC)CC)C>C1COCC1.CN(C)C1C=CN=CC=1>[CH2:1]([NH:8][CH2:9][CH:10]([CH2:21][O:22][Si:27]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:29])[CH3:28])[CH:11]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[C:15]([Cl:20])[CH:14]=1)[OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 66975085HCID 66975085, compound

Product 1

HCID 66975486HCID 66975486, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1RS,2SR)-2-[(benzylamino)methyl]-1-(3-chloro-4-fluorophenyl)propane-1,3-diol (the above-mentioned crude product) in THF (170 ml) were added tert-butylchlorodimethylsilane (5.38 g), triethylamine (7.1 ml) and 4-(dimethylamino)pyridine (415 mg) under ice-cooling, and the mixture was stirred at room temperature for 18 hr. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate. The diluted solution was washed with distilled water, saturated aqueous sodium hydrogen carbonate and brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the title compound (14.1 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, saturated aqueous sodium hydrogen carbonate and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-01f4a16d9eb8493ebacd5d1722cd375b
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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