Triethylamine → HCID 23160669, compound

HRID 1360390Notes

Reaction equation

HRID 1360390 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:12][CH2:11][C:10]2=[O:13])=[CH:5][CH:4]=1.FC(F)(F)S(O)(=O)=O.C(N(CC)CC)C.[BH4-].[Na+]>ClCCCl.C(O)C>[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][CH:4]=1)[NH:9][CH2:12][CH2:11][CH:10]2[OH:13]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 62406Trifluoromethanesulfonic acidHCID 4311764Sodium borohydrideHCID 15421643HCID 15421643, compound

Product 1

HCID 23160669HCID 23160669, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 702EthanolSolvent

Procedure

1-[4-(Trifluoromethyl)phenyl]azetidin-2-one (2.3 g, 10.7 mmol) was dissolved in 1,2-dichloroethane (20 mL), trifluoromethanesulfonic acid (1 mL) was added at 0° C., and the mixture was stirred at room temperature for 30 min. Triethylamine (2.2 mL) was added to the reaction mixture, and the mixture was worked-up according to a conventional method to give a crude product. The obtained crude product was dissolved in ethanol (10 mL), sodium borohydride (0.81 g, 21.4 mmol) was added, and the mixture was stirred for 4 hrs. The solvent was evaporated and the residue was purified by silica gel column chromatography to give the title compound (0.35 g, 1.6 mmol, 15%).

Workup

  1. customto give a crude product
  2. customThe obtained crude product
  3. stirringthe mixture was stirred for 4 hrs
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-25014553b19c40bc9435840abef1e382
Source dataset
uspto-grants-2011_02
Patent number
US07879863B2

Reaction notes

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