Sodium borohydride → HCID 17857898, compound

HRID 1374440Notes

Reaction equation

[Br-].[CH2:2]([N+:9]1[CH:14]=[C:13]([C:15]([O:17][CH3:18])=[O:16])[CH:12]=[CH:11][C:10]=1[CH3:19])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[BH4-].[Na+].C(OCC)(=O)C.[Cl-].[Na+].O>CO.O>[CH2:2]([N:9]1[CH:10]([CH3:19])[CH2:11][CH:12]=[C:13]([C:15]([O:17][CH3:18])=[O:16])[CH2:14]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 1-benzyl-5-(methoxycarbonyl)-2-methylpyridinium bromide (3.2 g, 9.9 mmol) in methanol (50 ml) was added at −70° C. a solution of sodium borohydride (0.75 g, 20 mmol) in water (10 ml). The mixture was raised to 0° C. and stirred for 20 minutes. The reaction mixture was added to ethyl acetate/brine and the mixture was separated with a separating funnel. The aqueous layer was extracted twice with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate and the solvent was removed in vacuo. The residue (2.34 g) was purified with silica gel (60 g) chromatography (hexane/ethyl acetate=4/1) to give methyl 1-benzyl-6-methyl-1,2,5,6-tetrahydro-3-pyridinecarboxylate (2.05 g, 84%).

Workup

customthe mixture was separated with a separating funnel
extractionThe aqueous layer was extracted twice with ethyl acetate
washThe organic layer was washed with a saturated aqueous sodium chloride solution
dry with materialdried over magnesium sulfate
customthe solvent was removed in vacuo
customThe residue (2.34 g) was purified with silica gel (60 g) chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record: ord-bd337c853a7c4c378d79f4d812940941
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07163936B2

Reaction notes

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