Ammonium Chloride → ethyl 2-[5-(methylsulfanyl)pyridin-2-yl]-3-(tetrahydro-2H-pyran-4-yl)propanoate

HRID 1881916Notes

Reaction equation

HRID 1881916 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([C:9](=[CH:15][CH:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:7][CH:8]=1.[BH4-].[Na+].[Cl-].[NH4+]>CO>[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]([CH2:15][CH:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 68433868ethyl 2-[5-(methylsulfanyl)pyridin-2-yl]-3-(tetrahydro-2H-pyran-4-yl)-2-propenoate

Product 1

HCID 59331616ethyl 2-[5-(methylsulfanyl)pyridin-2-yl]-3-(tetrahydro-2H-pyran-4-yl)propanoateYield 59.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 2-[5-(methylsulfanyl)pyridin-2-yl]-3-(tetrahydro-2H-pyran-4-yl)-2-propenoate (2.41 g) in methanol (20 mL) was added sodium borohydride (890 mg), and the mixture was stirred at room temperature for 3 hr. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium to sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and the title compound (1.44 g, yield 59%) was obtained as a yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (2:1, volume ratio).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium to sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bee9a53c896846b79b7d0fc0d28d85a3
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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