Formaldehyde → HCID 10590942, compound

HRID 5106

Reaction equation

HRID 5106 reaction equation
C=O.[C:3]([BH3-])#[N:4].[Na+].[CH2:7]([NH:9][C:10]([C@@H:12]1[CH2:16][C@H:15]([S:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH2:14]N1)=[O:11])[CH3:8].[OH-].[Na+].[Cl-].[Na+]>C(#N)C>[CH2:7]([NH:9][C:10]([C@@H:12]1[CH2:16][C@H:15]([S:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH2:14][N:4]1[CH3:3])=[O:11])[CH3:8]

Participants

7

Reactant 5

HCID 712FormaldehydeHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 14880286(2S, 4S)-2-Ethylcarbamoyl-4-(4-methoxybenzylthio)pyrrolidine

Product 1

HCID 10590942HCID 10590942, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3.43 ml of 35% formalin and 804 mg of sodium cyanoborohydride were added to a solution of 2.36 g of (2S, 4S)-2-ethylcarbamoyl-4-(4-methoxybenzylthio)-pyrrolidine dissolved in 42 ml of acetonitrile, and the mixture was stirred at room temperature for 40 minutes. At the end of this time, a 1N aqueous solution of sodium hydroxide was added, and the reaction mixture was poured into an aqueous solution of sodium chloride and extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography through silica gel (eluted with ethyl acetate) to afford 1.93 g of the title compound as colorless crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with an aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed by distillation under reduced pressure
  5. customThe residue was purified by column chromatography through silica gel (eluted with ethyl acetate)

Sources & evidence

ORD record
ord-0396738389f34b4993d50a9f35e708e2
Source dataset
uspto-grants-1993_09
Patent number
US05242914

Linked notes

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