2-Thiophenecarboxaldehyde → HCID 23369385, compound

HRID 1900575Notes

Reaction equation

HRID 1900575 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6].[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[CH:14]=O.[BH3-]C#N.[Na+]>CO>[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[CH2:14][NH:2][CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 73642-ThiophenecarboxaldehydeHCID 2734767Methyl 3-aminopropanoate hydrochlorideHCID 5003444Sodium cyanoborohydride

Product 1

HCID 23369385HCID 23369385, compoundYield 30.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirring 25 mL MeOH solution of 1.40 g (10 mmol) of methyl β-alaninate hydrochloride and 1.34 g (12 mmol) of thiophene carboxaldehyde was added 1.26 g (20 mmol) of NaCNBH3. After 1 hour, 25 mL of saturated KHCO3 was added to the reaction. The reaction mixture was then filtered, and the resulting filtrate was extracted with 50 mL of DCM. The organic layer was treated as described above in Example 7, and the residue was chromatographed to yield 0.60 g (30%) of product. Analysis calculated for C9H13NO2S (M.W. 199.27): C, 54.25; H, 6.58; N, 7.03. Found: C, 54.02; H, 6.63; N, 6.77.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. extractionthe resulting filtrate was extracted with 50 mL of DCM
  3. additionThe organic layer was treated
  4. customthe residue was chromatographed

Sources & evidence

ORD record
ord-ecc1fceb17e94b1a952921c6b978c15b
Source dataset
uspto-grants-1996_11
Patent number
US05576315

Reaction notes

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