2-Thiophenecarboxaldehyde → N-(2-Thienylmethyl)-β-alanine ethyl ester

HRID 1511613Notes

Reaction equation

HRID 1511613 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=O.C(N(CC)CC)C.Cl.[NH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].[BH4-].[Na+]>CO>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

6

Reactant 4

HCID 73642-ThiophenecarboxaldehydeHCID 8471TriethylamineHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 4311764Sodium borohydride

Product 1

HCID 14896429N-(2-Thienylmethyl)-β-alanine ethyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Thiophene aldehyde (11.2 g) was dissolved in 100 mL of methanol, then 12.1 g of triethylamine and 16.1 g of ethyl 3-aminopropionate hydrochloride were added thereto in this order and the mixture was stirred overnight at room temperature. The reaction solution was cooled down to 0° C., 2.27 g of sodium borohydride was slowly added thereto little by little and the mixture was stirred at room temperature for 1 hour.

Workup

  1. temperatureThe reaction solution was cooled down to 0° C.
  2. stirringlittle by little and the mixture was stirred at room temperature for 1 hour

Sources & evidence

ORD record
ord-bfd4f80a6bf3423fb385279c8056c432
Source dataset
uspto-grants-2012_07
Patent number
US08217031B2

Reaction notes

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