Acetic Acid → HCID 57501273, compound

HRID 2114341Notes

Reaction equation

HRID 2114341 reaction equation
CN.[Br:3][C:4]1[CH:5]=[C:6]([C:10](=O)[CH2:11][N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:7]=[CH:8][CH:9]=1.[C:18]([BH3-])#[N:19].[Na+].C(O)(=O)C>C1COCC1>[Br:3][C:4]1[CH:5]=[C:6]([CH:10]([NH:19][CH3:18])[CH2:11][N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6329MethylamineHCID 5003444Sodium cyanoborohydrideHCID 43227580HCID 43227580, compound

Product 1

HCID 57501273HCID 57501273, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.0 M methylamine solution in THF (55 mL, 110.0 mmol) was added to a solution of 1-(3-bromophenyl)-2-(1-pyrrolidinyl)ethanone (7.40 g, 27.62 mmol) in anhydrous THF (30 mL) at room temperature. The reaction mixture was stirred for 1 h and then sodium cyanoborohydride (5.21 g, 82.86 mmol) and acetic acid (3 mL) were added. The resulting reaction mixture was continually stirred at room temperature for 96 h until the starting material was consumed completely. Saturated K2CO3 solution (100 mL) was added and after stirring for 15 min, the solution was extracted with ethyl acetate (2×80 mL). The organic layers were combined, dried over Na2SO4, and concentrated. The resulting residue was isolated by column chromatography on silica gel (MeOH/EtOAc, 1:10) to yield the title compound as a yellow oil (3.75 g, 48%), MS (ES) m/e 283[M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. stirringwas continually stirred at room temperature for 96 h until the starting material
  3. customwas consumed completely
  4. additionSaturated K2CO3 solution (100 mL) was added
  5. stirringafter stirring for 15 min
  6. extractionthe solution was extracted with ethyl acetate (2×80 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe resulting residue was isolated by column chromatography on silica gel (MeOH/EtOAc, 1:10)

Sources & evidence

ORD record
ord-89344b6e86c04c50874d110f700bb063
Source dataset
uspto-grants-2008_10
Patent number
US07432258B2

Reaction notes

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