Iodoethane → HCID 46208105, compound

HRID 2041885Notes

Reaction equation

HRID 2041885 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2([OH:13])[CH2:12][NH:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8].I[CH2:15][CH3:16]>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([C:9]2([OH:13])[CH2:12][N:11]([CH2:15][CH3:16])[CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 6340IodoethaneHCID 65439120HCID 65439120, compound

Product 1

HCID 46208105HCID 46208105, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-(3,4-difluorophenyl)azetidin-3-ol (0.3 g, 1.62 mmol) triethylamine (0.68 ml, 4.87 mmol) and iodoethane (0.19 ml, 2.44 mmol) in tetrahydrofuran (15 ml) was stirred at ambient temperature for 15 h. The solvent was evaporated and aqueous hydrochloric acid (50 mL. 10%) was added and the mixture was washed with tert-butyl methyl ether (2×50 ml). The aqueous phase was made basic by addition of aqueous sodium hydroxide (5 M) and extracted with tert-butyl methyl ether (2×50 ml). The combined organic phase was dried (Na2SO4) and evaporated under reduced pressure to give the crude product (0.26 g). Purification by flash column chromatography on silica gel (ethyl acetate/methanol 1:1) gave 0.2 g (58%) of the title compound. The amine was converted to the fumaric acid salt and recrystallized from methanol/diethyl ether: M.p. 177-179° C. MS m/z (relative intensity, 70 eV) 213 (M+, 1), 141 (86), 127 (45), 114 (58), 58 (bp).

Workup

  1. customThe solvent was evaporated
  2. additionaqueous hydrochloric acid (50 mL. 10%) was added
  3. washthe mixture was washed with tert-butyl methyl ether (2×50 ml)
  4. additionThe aqueous phase was made basic by addition of aqueous sodium hydroxide (5 M)
  5. extractionextracted with tert-butyl methyl ether (2×50 ml)
  6. dry with materialThe combined organic phase was dried (Na2SO4)
  7. customevaporated under reduced pressure
  8. customto give the crude product (0.26 g)
  9. customPurification by flash column chromatography on silica gel (ethyl acetate/methanol 1:1)

Sources & evidence

ORD record
ord-28b770970acd454f9c577f374de8aed2
Source dataset
uspto-grants-2013_11
Patent number
US08586572B2

Reaction notes

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