Sodium cyanoborohydride → HCID 59442007, compound

HRID 1014180Notes

Reaction equation

HRID 1014180 reaction equation
[Br-].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:13]2[CH:14]=[N+:15]([CH2:19][CH:20]=[CH2:21])[CH:16]=[CH:17][CH:18]=2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11].[BH3-]C#N.[Na+]>CO>[CH3:2][O:3][C:4]1[CH:5]=[C:6]([C:13]2[CH2:14][N:15]([CH2:19][CH:20]=[CH2:21])[CH2:16][CH2:17][CH:18]=2)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11]

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 67316339HCID 67316339, compound

Product 1

HCID 59442007HCID 59442007, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 3-[3-(methyloxy)-4-nitrophenyl]-1-(2-propen-1-yl)pyridinium bromide (28.2 g, 80.0 mmol) in MeOH (200 mL) was added NaBH3CN (21.1 g, 320.0 mmol). The reaction was heated to 65° C. and stirred for 72 h. The cooled solution was concentrated to remove MeOH, and to the residue was added saturated aq. NaHCO3 (100 mL). After extraction with Ethyl acetate (2×100 mL), concentration, and drying (Na2SO4), purification by silica chromatography afforded 5-[3-(methyloxy)-4-nitrophenyl]-1-(2-propen-1-yl)-1,2,3,6-tetrahydropyridine (11.0 g, 50%). ESIMS (M+H)+=275.

Workup

  1. concentrationThe cooled solution was concentrated
  2. customto remove MeOH
  3. additionto the residue was added saturated aq. NaHCO3 (100 mL)
  4. extractionAfter extraction
  5. concentrationwith Ethyl acetate (2×100 mL), concentration
  6. customdrying
  7. custom(Na2SO4), purification by silica chromatography

Sources & evidence

ORD record
ord-fbb2380104f14e9d99b146ab83b6f041
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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