Myosmine → 3-(Pyrrolidin-2-yl)pyridine

HRID 384838

Reaction equation

HRID 384838 reaction equation
[CH:1]1[CH:6]=[N:5][CH:4]=[C:3]([C:7]2[CH2:11][CH2:10][CH2:9][N:8]=2)[CH:2]=1>[Pd].CO>[CH2:10]1[CH2:9][NH:8][CH:7]([C:3]2[CH:2]=[CH:1][CH:6]=[N:5][CH:4]=2)[CH2:11]1

Participants

4

Reactant 1

HCID 442649Myosmine

Product 1

HCID 4123-(Pyrrolidin-2-yl)pyridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent2×

Procedure

(J. Org. Chem., 1982, 47, 4165-4167). Hatton et al. used palladium on activated carbon in methanol to reduce myosmine labeled with stable isotope, [6−2H]-myosmine to [6−2H]-nornicotine (J. Label Compd. Radiopharm. 2009, 52, 117-122). After screening a number of catalysts, we selected palladium on carbon with methanol as medium. After general workup, the pure (R,S)-nornicotine was isolated by high vacuum distillation in high yields and high purity. Conversion of (R,S)-nornicotine to (R,S)-nicotine was carried out by N-methylation using formaldehyde and formic acid as reported in the literature (J. Amer. Chem. Soc., 1993, 115, 381-387).

Sources & evidence

ORD record
ord-965ecdeef1a142b68b6f350749f22210
Source dataset
uspto-grants-2013_02
Patent number
US08367837B2

Linked notes

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