Allyl bromide → HCID 25143955, compound

HRID 1931832Notes

Reaction equation

HRID 1931832 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2([OH:14])[CH2:13][CH2:12][NH:11][CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[CH:22]=[CH2:23].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[CH2:23]([N:11]1[CH2:12][CH2:13][C:9]([C:4]2[CH:5]=[C:6]([F:8])[CH:7]=[C:2]([F:1])[CH:3]=2)([OH:14])[CH2:10]1)[CH:22]=[CH2:21]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 63585886HCID 63585886, compound

Product 1

HCID 25143955HCID 25143955, compoundYield 23.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

In a sealed tube a mixture of enantiomer E2 of 3-(3,5-difluorophenyl)pyrrolidin-3-ol (0.29 g, 1.45 mmol), acetonitrile (15 mL), potassium carbonate (0.4 g, 2.9 mmol) and allylbromide (0.13 mL, 1.59 mmol) was heated at 60° C. for 2 h. Aqueous sodium carbonate (10%, 5 mL) was added and the aqueous phase was extracted with ethyl acetate (2×50 mL). The combined organic phase was dried (Na2SO4) and evaporated. Purification by flash chromatography on silica gel (ethyl acetate/methanol, 7:1) gave the title compound (0.08 g). [α]D=−20.3° (methanol). The amine was converted to the oxalic acid salt and recrystallized from ethanol/diisopropyl ether: M.p. 102-103° C.; MS m/z (relative intensity, 70 eV) 239 (M+, 22), 83 (bp), 198 (52), 82 (33), 84 (29), 113 (27).

Workup

  1. extractionthe aqueous phase was extracted with ethyl acetate (2×50 mL)
  2. dry with materialThe combined organic phase was dried (Na2SO4)
  3. customevaporated
  4. customPurification by flash chromatography on silica gel (ethyl acetate/methanol, 7:1)

Sources & evidence

ORD record
ord-e97749d2dde74592b7660e218a4ae8f7
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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