Butyl bromide → HCID 25143819, compound

HRID 1931831Notes

Reaction equation

HRID 1931831 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)[CH2:22][CH2:23][CH3:24].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[CH2:21]([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)[CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 8002Butyl bromideHCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 63585886HCID 63585886, compound

Product 1

HCID 25143819HCID 25143819, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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 n-butylbromide (0.15 mL, 1.59 mmol) was stirred at ambient temperature for 5 h and then 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 (0.175 g). [α]D=−19.8° (methanol). The amine was converted to the oxalic acid salt and recrystallized from methanol/diisopropyl ether: M.p. 146-147° C.; MS m/z (relative intensity, 70 eV) 255 (M+, 6), 212 (bp), 98 (46), 182 (35), 57 (29), 127 (13).

Workup

  1. waitat 60° C. for 2 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, 7:1)

Sources & evidence

ORD record
ord-df9ffeb905294b8f817866b2e839c8c6
Source dataset
uspto-grants-2012_05
Patent number
US08188301B2

Reaction notes

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