Acetonitrile → HCID 25143956, compound

HRID 1931833Notes

Reaction equation

HRID 1931833 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:15](=[O:18])([O-])[O-].[K+].[K+].C(=O)([O-])[O-].[Na+].[Na+].[C:27](#N)[CH3:28]>>[F:1][C:2]1[CH:3]=[C:4]([C:9]2([OH:14])[CH2:13][CH2:12][N:11]([CH2:27][CH2:28][O:18][CH3:15])[CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 63585886HCID 63585886, compound

Product 1

HCID 25143956HCID 25143956, compound

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 2-bromoethylmethyleter (0.145 mL, 1.55 mmol) was stirred at ambient temperature for 4 h. and then at 80° C. for 1 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, 10:1) gave the title compound (0.157 g). [α]D=−18.9° (methanol). The amine was converted to the oxalic acid salt and recrystallized from ethanol/diisopropyl ether: M.p. 130-131° C.; MS m/z (relative intensity, 70 eV) 257 (M+, 2), 212 (bp), 182 (52), 127 (12), 213 (12), 58 (8).

Workup

  1. waitat 80° C. for 1 h
  2. extractionthe aqueous phase was extracted with ethyl acetate (2×50 mL)
  3. dry with materialThe combined organic phase was dried (Na2SO4)
  4. customevaporated
  5. customPurification by flash chromatography on silica gel (ethyl acetate/methanol, 10:1)

Sources & evidence

ORD record
ord-2b5deb201d0643ba8978e0f8400eecaf
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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