Triethylamine → HCID 69347213, compound

HRID 855234Notes

Reaction equation

HRID 855234 reaction equation
[C:1]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[C:14]([O:18][C:19](=[O:23])[CH2:20][CH2:21][NH2:22])([CH3:17])([CH3:16])[CH3:15].C(N(CC)CC)C.[BH4-].[Na+]>CO.O>[C:14]([O:18][C:19](=[O:23])[CH2:20][CH2:21][NH:22][CH2:9][C:8]1[CH:11]=[CH:12][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 703244-tert-ButylbenzaldehydeHCID 4311764Sodium borohydrideHCID 16218890Tert-butyl 3-aminopropanoate hydrochloride

Product 1

HCID 69347213HCID 69347213, compoundYield 79.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

3.24 g (20 mmol) of 4-tert-butyl benzaldehyde, 3.63 g (20 mmol) of beta-alanine tert-butylester hydrochloride and 2.22 g (22 mmol) of triethyl amine were dissolved in 20 ml methanol and stirred at rt for 1 h. 1.11 g (30 mmol) of sodium borohydride were added in portions under nitrogen and the reaction mixture was stirred for 2 h at rt after complete addition. Water was added and the solvent was evaporated. The residue was extracted twice with diethyl ether. The combined organic layers were washed twice with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and the solvent was evaporated. The residue was purified by column chromatography (silica gel, diethyl ether) to yield 4.62 g (79%) product as a colorless oil. 1H NMR (DMSO-d6, 300 MHz): δ 7.34 (d, 2H), 7.25 (d, 2H), 3.76 (s, 2H), 2.86 (t, 2H), 2.45 (t, 2H), 1.44 (s, 9H), 1.31 (s, 9H).

Workup

  1. stirringthe reaction mixture was stirred for 2 h at rt
  2. additionafter complete addition
  3. customthe solvent was evaporated
  4. extractionThe residue was extracted twice with diethyl ether
  5. washThe combined organic layers were washed twice with saturated aqueous sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was purified by column chromatography (silica gel, diethyl ether)

Sources & evidence

ORD record
ord-a7b1b5ca5fff45dfafd692ec0a1ba1d0
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

Loading…